


The Hooker Assassin

by GatorGirl2016



Category: Supernatural
Genre: Alternate Universe - Modern Setting, Anal Fingering, Anal Sex, Angst, Angst with a Happy Ending, Assassin Dean Winchester, Attempted Murder, Bottom Dean Winchester, Businessman Castiel, Explicit Language, Explicit Sexual Content, F/M, Falling In Love, Love Confessions, M/M, Multi, Murder, Oral Sex, Pretty Woman References, Prostitute Dean Winchester, Seduction, Smut, Strangers to Lovers, Top Castiel (Supernatural), Top Castiel/Bottom Dean Winchester
Language: English
Status: Completed
Published: 2020-04-29
Updated: 2020-05-02
Packaged: 2021-03-01 23:27:01
Rating: Explicit
Warnings: Graphic Depictions Of Violence
Chapters: 3
Words: 32,804
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23915287
Author URL: https://archiveofourown.org/users/GatorGirl2016/pseuds/GatorGirl2016
Summary: Dean is an assassin looking for a case but pretending to be a hooker. He comes across Cas and the man ends up giving him a case unknowingly. Dean and Cas spend a week in each other's presence and slowly develop feelings for one another. What happens though when Cas finds out the truth about Dean's work? Based loosely off the movie Pretty Woman because it's what inspired this work.
Relationships: Castiel/Dean Winchester, Ellen Harvelle/Bobby Singer
Comments: 4
Kudos: 89





	1. Introductions

**Author's Note:**

> Here is another story for all you lovely people. This was inspired by the movie Pretty Woman and if you've never seen it, I would recommend it. I really hope you guys enjoy this story as much as I enjoyed writing it.

Dean moaned in fake pleasure as the man above him thrust deep into his body and orgasmed, filling the condom that Dean had insisted he wear. The blonde grimaced as the man slumped against him, breathing hot pungent breath into his face. The man panted harshly, his eyes closed and therefore never saw Dean reach under the pillow and pull out the knife he had stashed there earlier. The man’s eyes opened wide in shock as the blade was thrust into his throat.

The dying man grabbed at his throat, blood pouring over his fingers and pooling onto Dean’s chest and stomach. The man above started making gargling noises as he was choking on his own blood. His eyes locked with Dean’s and the blonde smirked as he yanked the knife from the man’s throat. His eyed widened more as blood gushed from the hole in his throat. Dean watched as his eyes rolled back in his head before slumping forward.

The blonde shoved the lifeless body off him. Blood was still pouring out the wound and the sheets and Dean were coated in the bright red liquid. He wiped his blade on a corner of the sheet that wasn’t stained red before standing up and stretching. He walked to the bathroom, uncaring of the blood dripping off his body. He turned the shower on and waited for the water to warm up. Once the bathroom mirror was fogged due to all the steam, he stepped under the hot spray.

Dean sighed as the water pounded against his muscles. He was more tense than he had realized. It was probably due to the past six days of trying to get the dead guy to bring him back to a hotel. It had taken Dean longer than he had expected to seduce the man, but he had got his prize in the end. The children of this small town would no longer have to be afraid of being snatched from their parents, never to return home.

Dean hung his head and watched the water run down the drain. He stayed in the shower until the red water turned bright pink and finally running clear indicating all the blood had been washed away. Dean quickly washed up before stepping out and wrapping a towel around his waist. He walked back into the bedroom, water droplets still clinging to his skin. He paid no attention to the body as he headed for his clothes piled on the floor. He grabbed his pants and pulled his cell phone out. He hit the call button for the first contact on his speed dial. He waited two rings before the call was picked up.

“Finally, you call me! Dude, you’re an hour later than you said you would be,” Charlie berated him.

Dean smiled, “Sorry my queen but the dude wanted to take his sweet time about coming back to the room. He wanted to show off his hot fuck for the night.”

“Hope you enjoyed yourself, he looked like he would be a good lay.”

The blonde frowned, “Let’s just say I think he abducted kids to compensate for his lack of a package. So, yeah pretty shitty fuck if you ask me.”

“And you wonder why I’m only into females. Don’t have to worry about a woman lacking in that department,” Charlie gloated.

Dean rolled his eyes, “Whatever. Anyway, he’s dead so can you send the cleanup crew?”

“Psshh, what do you take me for an amateur? As soon as you called, I alerted the guys. They should be there in about ten minutes. You going to stick around or make yourself scarce?”

Dean walked over to the table in the room and pulled out a chair before sitting heavily, “I’ll be gone. Gonna head to Ellen’s and have a couple drinks. You wanna join me?”

“Sorry, can’t. Benny is finally closing in on that rapist he’s been tracking for the past couple weeks. I’m on call in case something goes bad,” the redhead explained.

The blonde scrubbed a hand down his face before replying, “It’s fine. Maybe next time. I’m gonna get going so I can be gone by the time cleanup gets here. Talk to you later Charlie.”

“Bye Dean and stay safe.”

He smiled, “I always do my queen.”

He hung up on his friend before grabbing his clothes and getting dressed. Once he was fully clothed, he picked his knife off the bed and slid it back into his boot. He squatted down and pulled his gun from under the bed before tucking it against his lower back. He slipped his leather jacket on. He grabbed the dude’s wallet and took the money out of it before slipping it into his pocket. He dropped the wallet on the ground and headed towards the window leading to the fire escape. He quickly made his way down the rickety metal steps. Once his feet touched the concrete, he headed towards where he had parked his car.

Five minutes later and his vehicle came into site. Once he was close enough, he rubbed his hand lovingly down the Impala’s side before unlocking the door and sliding behind the wheel. “C’mon Baby, let’s blow this town.” He pulled out the parking lot and headed out of town, driving towards home.

An hour later, the Impala pulled up to The Roadhouse, a bar owned by his aunt Ellen and a central location for all Hunter Corp assassins. Dean put Baby in park before heading inside. As he walked through the door, a few heads turned and looked at him. Some people smiled, some raised their glasses, while others scowled. Over the years, Dean had racked up some pretty major enemies mostly because he was the go-to for Hunter Corp. A lot of others had lost business because of Dean. The blonde just smirked, if the others wanted more jobs than maybe they should get better at them.

The assassin walked towards the bar and took one of the empty stools. He had barely sat down before a bottle of whiskey was placed in front of him. He looked up to see Jo Harvelle standing in front of him, a grin plastered on her face.

“Hey Winchester, I thought you said you’d be back days ago.”

Dean opened the bottle and took a gulp. He sighed as the liquid burned his throat as it slid down. He smacked his lips in appreciation of the taste.

“Yeah, well stupid bastard was very particular in who he took home. I’ve spent the last week flirting with the slimeball trying to get him to take me back to a hotel. Finally managed it tonight,” the man said proudly knowing one less criminal was out preying on innocents.

“Well, you got him, that’s all that matters. You want anything to eat,” the blonde offered.

“Yeah, I’ll take my usual. You know if Ellen has any jobs for me,” Dean asked casually.

The blonde waitress turned around and hollered Dean’s order to the kitchen: a bacon cheeseburger, all the way with extra crispy curly fries. She turned back around to face her adopted cousin. Her mother, Ellen, wasn’t really Dean’s aunt but she had cared for him ever since his parents had been murdered and his brother had been kidnapped.

Ellen’s husband, Bobby had immediately went searching for Dean’s younger brother, Sam. By the time he found him, Sam’s body had been cold and broken. His killers had never been found and it was Dean’s greatest regret. It was Sam’s death that drove Dean into the life he led now. The young man had insisted his uncle train him to be an assassin just like him. Bobby had refused until he had found Dean training with another assassin named Benny.

The blonde had gone on his first solo mission the day he turned eighteen. His target was dead within two days and upon his return, he was officially inducted into Hunter Corp which was an underground group funded by the government. Its members were hired to take care of cases that the government wanted dealt with but didn’t want their hands getting dirty.

After joining, Dean became relentless, racking up kills by the dozen. He rose to the top of Hunter Corp’s list of assassins within three years. He skills weren’t the only thing that made him successful. His age and looks helped a lot. Dean had learned how to use his body and his looks to get close to his marks. Throughout the business, he was known as Hooker. Ellen and Bobby didn’t approve of his methods but if allowing his marks to fuck him got him close enough to kill them, then so be it.

Jo sighed, “Dean, you just got home and you’re already looking for another hit? Do you ever take a break?”

The blonde glared, “You already know the answer to that Jo. A night’s sleep and I’ll be ready to head out again.”

The waitress frowned, “Mom and Dad aren’t going to be happy. They really want you to take a vacation. Dad said you’ve been overworking yourself again and Mom agrees.”

The assassin shrugged, “Yeah, well, I can make my own decisions and I say I’m fine.”

The waitress placed a hand on top of Dean, “Hey, I know it’s that time of year again, but you can’t keep doing this. You’re going to run yourself ragged and that can get you killed.”

The assassin glared, “I said I’m fine Jo.”

She sighed knowing she wasn’t going to win this battle. The week leading up to the anniversary of Mary, John, and Sam Winchester’s deaths, Dean would overwork himself to the bone. He thought if he could keep his mind focused on his targets, he wouldn’t be consumed by the grief he still felt. Dean had cried his last tear for his family long ago but the grief he carries inside of him will last forever. That grief drove him, made him kill villain after villain. Dean had vowed long ago to clean the streets of as many murderers, rapists, abusers, and any other low life scum so that what happened to his family would never happen again.

“Whatever, Dean. Mom and Dad already went to bed, so you’ll have to wait until tomorrow to talk to them.” She walked to the kitchen window when she heard the bell. She grabbed the blonde’s food before placing it in front of him. She grabbed a bottle of beer and set it on the counter before going to serve other customers.

Dean watched her leave but said nothing. He knew they would never see eye to eye on that particular topic. She had never lost family and didn’t know what it felt like. She had no idea of the pain he relived every year, the reminder that his parents and brother were dead while he still lived. He had lost them when he was only ten years old. The day of their funerals had been the only time he had cried for them. Ever since then, he had drowned his feelings in his work. His never-ending rage had fueled him and allowed him to become the top assassin in HC. 

The man ate his meal in silence. Once he finished his beer, he pulled his wallet out his pocket and dropped two twenties on the counter. Ellen didn’t like him paying but she worked hard, and she deserved to be compensated. He took one last look at Jo before heading behind the bar and upstairs to his bedroom.

The sunlight filtering through the curtains roused Dean from his sleep the following morning. He rubbed the sleep from his eyes before crawling out of bed and heading to the bathroom. Once he relieved his full bladder and brushed his teeth, he pulled some clothes from his dresser and got dressed.

He walked downstairs and headed towards the kitchen. He found Bobby, Ellen, and Jo standing at the counter, eating breakfast. He walked to the coffee pot and poured himself a cup. He took a sip and let the steaming liquid slide down his throat.

Jo scrunched her nose, “How you drink that black is beyond me. There’s a plate of food in the mic for you.”

He nodded his head in acknowledgement. He grabbed his food before joining his family at the counter. Ellen looked up and nodded in his direction, “Charlie checked in this morning. Said you guys finally took care of Marco.”

Dean swallowed his bite before replying, “Yes ma’am. Sorry it took so long. So, what ya got next?”

Ellen and Bobby shared a look before his uncle said, “We don’t. Dean, it’s time you took a break. You’ve been doing this job for nine years straight. The only time you aren’t working is when you’re asleep or injured. Hell, half the time I think I’m gonna have to handcuff you to the bed to keep you from hurting yourself further. It’s time to take a break son.”

The blonde dropped his fork, anger flaring in his eyes, “I don’t need a damn break Bobby. I need another target!”

Ellen spoke up, “Dean, you’re running yourself into the ground. We’ve all been noticing it. You’re exhausted and it’s starting to affect your work. It’s never taken a week for you to drop a target.”

Dean glared at her, “Like I told Charlie and Jo, the bastard was selective, and I had to get him to trust me before he’d fuck me so I could kill him.”

“Son, we’re just trying to look out for you. We don’t want you getting hurt. Just take a week off, that’s all we’re asking,” Bobby tried to make reason with his boy.

“I said no and if you won’t find me a hunt, then I’ll find one on my own,” he stated coldly before turning on his heel and walking out. He ignored the calls behind him. He rushed up to his room and packed everything within sight. He heard knocking on his door but he had locked it so no one could get in.

“Dean, open up please. Mom and Dad just want you to take better care of yourself. Please, Dean, just listen to them,” Jo begged from the other side of the door.

He threw his toothbrush and deodorant in the bag before zipping it closed. He opened the window and crawled out. He grabbed his bag, took one last look at his bedroom door, and climbed down to his car. He opened the trunk and dropped the bag inside before getting behind the steering wheel. He stomped on the gas pedal and tore out the parking lot. He looked in the review mirror and saw his family staring. He knew he was hurting them, but he forced himself to keep driving.

Dean drove for a couple days, not caring where he was going. He finally slowed down as he came upon the outskirts of Beverly Hills. He drove until he came to the first hotel he spotted. He parked Baby and went inside to book a room. He decided to just rent for a week and go from there. He walked to the room and once inside, dropped his bag on the bed.

He pulled his laptop out and spent the next few hours searching for any crime in the area. He gave a frustrated sigh when all his searches turned out to be nothing serious. The usual petty crime and theft but nothing major. He wondered if another HC assassin was here or had recently been in the area. He closed his laptop in agitation. He looked around and realized just how late it had gotten. Late afternoon rays were streaming through the window. His stomach growled, angry at having missed lunch.

Dean decided to go out for an early dinner and then figured he’s hit up a local bar afterwards. He searched through his bag and pulled out some more seductive clothing. He changed into a pair of tight black pants that accentuated his assets. He threw on a dark green Henley that brought his eyes out and was just on this side of being too small. He slipped his feet into his black leather boots that rose to mid-calf. He slipped his knife into the right boot, choosing to leave his gun behind for the night. The knife was all he needed usually. He slipped his leather jacket on before heading out.

He saw a diner down the street and chose to just walk instead of drive Baby. It was only about ten minutes later before he walked through the doors and took a seat at a secluded table in the corner. Immediately a waitress walked up and placed a menu in front him.

“Hey there, my name is Daisy and I’ll be your server tonight. Our special is the meatloaf and we have pecan pie for desert. Do you know what you’d like to drink,” she introduced herself, a polite smile on her face.

“I’d like a Bud Light please. I’ll go ahead and order the meatloaf and ring me up for a slice of pecan too,” Dean replied as he picked the menu up and handed it back to her.

She nodded, “Absolutely. I’ll have your beer back to you in a minute.”

The assassin flashed her a smile as she walked away. Dean quirked an eye as he looked at her retreating form. “Nice ass,” he muttered under his breath.

He had come to find a new target but maybe a night of fun was in order. Dean didn’t care one way or the other who he fucked, and he let fuck him. As long as there was protection, he would do it all.

The waitress returned and dropped his beer off before walking away to help other customers. Dean heard his phone go off and he pulled it out. It was a message from Charlie.

_“Dean, why are you in Hollywood? I thought you were going back to Ellen’s.”_

_“I did and I left this morning.”_

_“Why, Ellen nor Bobby asked me to find you another case, so I know they didn’t give you a debriefing.”_

_“They wanted me to take a vacation Charlie! A vacation, when have I ever taken a vacation? I don’t need a damn vacation; I need another fucking target. They wouldn’t give me one, so I decided to come find my own.”_

_“That’s their point though. You never quit working. Everybody needs a break even if it’s just a few days off, but you don’t even do that.”_

_“I’m fine Charlie, I don’t need a break especially this time of year. Now, could you tell me if there are any targets in Beverly Hills?”_

The waitress returned and set Dean’s plate down. “Is there anything else I can get for you?”

Dean gave her a bright smile, “No, sweetheart, that’s it, thanks.”

“Alright, well if you do need anything, let me know.”

Dean watched her walk away before going back to his phone. He frowned at the message.

_“No.”_

_“No, there isn’t a case?”_

He took a bite of his meatloaf as he waited for Charlie’s reply. He had another three forkfuls before he felt his cell vibrate. He looked at the message and fought to not slam the phone down.

_“No, I’m not telling you. I agree with Ellen and Bobby. You need a break!”_

_“Dammit Charlie! I already told you I don’t need a break. I’m going to find a target whether you tell me or not so why not just help out?”_

_“I said no Dean, find your own target. Maybe you’ll be shit at it and you will end up taking a few days off anyway.”_

_“Fat chance. I can find my own mark thank you very much.”_

_“Whatever, text me in a week and maybe I’ll have a case for you.”_

Dean dropped his cell on the table, a frown on his face. Why did everybody insist he needed a vacation all of a sudden? He’s never slowed down before so why would he now? He shook his head before digging back into his dinner. He finished his beer and waited for the waitress to bring his pie. He didn’t have to wait long.

“Here’s your pie. Would you like another beer?”

“Sure, why not?”

“I’ll have it right out.”

Dean waited for his drink before digging into his pie. It wasn’t the best he’d ever had; Ellen’s was way better but it was still pie. He dropped his fork before leaning back and sipping on his beer. He caught the waitress’s attention and waved his hand for her to come over.

“Yes sir?”

“Could I get my check sweetheart?”

Dean smirked as he noticed a twinge of disappointment cross her features before she replied, “Absolutely. Is there anything else I could get for you?”

Dean winked at her, “Nope, that will be all sweetheart.”

“I’ll be right back with the check then.”

She returned a moment later and laid three pieces of paper down. She quickly walked away, a blush evident on her cheeks. Dean looked at the papers. One was a receipt for the diner, one a receipt for him, and the last piece was a folded-up napkin.

On the napkin was written, “I get off at ten. Looking for some company later?”

The blonde smiled before pulling some cash out his wallet and dropping it on the table. He had considered having some fun but after his chat with Charlie, he was determined on finding a new target ASAP. He walked out without a second glance. He pulled his phone out and did a quick Google search for nearby clubs.

There was one about half a mile way, an easy walk for the young assassin. When he arrived, there was already a line forming at the entrance. Dean shrugged before going to the end. He only waited for about twenty minutes before he was being assessed by the bouncer and let in. He looked around. The lights were dimmed, giving the club an air of mysteriousness. He spotted the private section, easily identifiable by the golden ropes that sectioned it off from the rest of the club. The dance floor was already full of people grinding against one another in hopes of a fuck later one. Dean looked towards the bar and spotted an open seat. He made his way over.

“Give me three shots of vodka and a bottle of whiskey.”

“You want the cheap whiskey or the good stuff,” the bartender asked.

Dean smirked, “Give me the good stuff.” His target the other night had been rich, and Dean walked away with nearly a grand.

“Here you go, you want a tab?”

“Sure, why not?”

The bartender walked away as Dean threw his first shot back. He relished the burn of the liquid as it slid down his throat. It was exactly what he needed. He downed the second shot and shook his head slightly. He grabbed the third shot glass and held it to his lips as he perused the room. He was looking for anybody who stood out.

A shout near the door had him turning his head and setting his glass down. Six men walked into the club, shoving aside people waiting in line which has been the reason for the shouts. The bouncer told them they were VIP’s and had special access.

Dean watched the men carefully. All six of them were dressed in perfectly tailored suits and wore dark sunglasses, completely hiding their eyes. Two of the men looked like their suits were just barely containing the bulky muscles underneath. Both of those men were dark skinned and bald.

One of the men stuck out like a sore thumb as he walked in with a lollipop stuck in his mouth. He was also shorter than all the other men by nearly half a foot. His golden blonde locks were long and curled around his ears and at the bottom of his neck.

The other three men were all very similar in appearance. They were tall, six foot at least. They weren’t filled out with bulging muscles but there was no doubt they were in shape. They had broad shoulders which led into a tapered waist. The most discernable difference was their hair. Once man had blonde, one had dark brown, and one had hair as black as a raven.

Dean couldn’t take his eyes off the raven-haired man. Something about him drew Dean in. He felt his cock harden slightly in his pants. He knew he had to figure out this man’s name because Dean wanted him to be his next target. Even if the man didn’t need to be killed, Dean still desperately wanted to be fucked by him.

The six men walked up to the private section and were instantly allowed in. The assassin continued to watch them. The dark-skinned men were the bodyguards as they stayed standing as the other four men took seats. A waiter came up and asked for their drinks before scurrying off. He returned a few minutes later.

Dean couldn’t be certain, but it looked like lollipop dude had ordered a Piña colada, while the other three had ordered shots of some unknown drink. As the assassin watched he realized that raven-hair was the boss. Lollipop guy was too busy checking out the other patrons and wasn’t even participating in the discussion. Blondie and the brown-haired guy tried to not show submission, but Dean saw a few telltale signs. Blondie let his head dip slightly and the brown-haired guy lowered his eyes every once in a while. The raven, he kept his back straight, his shoulders relaxed, and he never bowed his head or lowered his eyes. Sometimes, people just exuded power without even trying.

Dean continued to stare as lollipop guy got up and went towards a group of three females. He pulled the sucker out of his mouth before saying something. Dean could only guess at what it was, as he and the women headed through another door leading further into the club. Blondie was the next to get up. He walked up to a young guy, not a day over twenty-one. He laid a hand on his shoulder before walking towards the secret door. Dean watched as the younger man stiffened before following. The brown-haired man was approached by a couple consisting of a man and a woman. He smiled before getting up and joining them as they walked to the door.

The only one left now was the raven and he didn’t seem too upset or surprised at his predicament. He threw a wad of bills on the table before getting up and walking out the private section and towards the exit. The bodyguards tried to follow him, but he motioned for them to leave him. Dean hastily pulled out some bills and threw them on the counter before getting up and quickly following the raven.

He followed the man for a few blocks until he came to a stop at a sports car. Dean gave a low whistle when he saw just what kind of car the man was standing beside. It was a Lamborghini Aventador S Coupe.

The man spun around, his eyes locking on Dean. In his hands a gun was pointed directly at the assassin’s chest. “Who are you?”

Dean held his hands up, “Woah, dude. Didn’t mean to spook you. Was just admiring your car. That’s a four-hundred-thousand-dollar automobile.”

The raven tilted his head and cocked an eyebrow, but the gun didn’t waver, “How did you even know it was here? Have you been following me?”

Dean looked scared on the outside, but on the inside, he was elated. This man could be a potential target if his first instinct was to pull a gun out. Dean knew he was going to have to do a little acting to calm this guy down and to get him to put the gun away.

He let a little fear leak into his voice, “Dude, could you put the gun down? I’m not gonna hurt you.”

“Then why did you follow me,” the man barked out.

Dean shrugged, “I saw you at that club back there.”

“And?”

“And, I thought you were good looking. I mean I’m pretty easy on the eyes and I’m kind of horny so I thought maybe I could interest you in a little fun time,” Dean winked and gave a little smile.

“You are propositioning me for sex based off the fact that we are two attractive men,” the gun lowered slightly.

“Well, I am a hooker and I have to make a living. You look like you’ve got money to spare. So, what do you say,” Dean asked cockily.

The gun lowered completely, “How do you even know that I prefer men to women?”

The assassin shrugged, “I didn’t but I thought it worth a shot.” Dean walked closer, “So, what do you say? Are you interested?” Dean licked his lips and smiled when he saw the other guy’s eyes follow the movement.

“And how much would it cost for these fun times as you call it,” the raven asked straightforward.

“A hundred bucks an hour sweetheart. So, you game?”

“A hundred bucks, is that a fair deal,” the guy asks with the head tilt again.

Dean shrugs, “Well, it’s about average. Charge too much and I don’t get enough clients but charge too little and I don’t make enough to live off. It’s a happy medium.”

Dean watches as the guy tucked his gun back into the holster hidden beneath his suit jacket. “And how much for the whole night?”

The assassin looks surprised, “The whole night? I don’t know of anyone who’s asked me to spend the whole night. You sure you got deep enough pockets for that?”

The other man smiled, “Like you said, I have a four-hundred-thousand-dollar car. Actually, it cost four hundred and twenty-five thousand dollars. This suit alone cost ten thousand. So, I think my pockets are deep enough.”

“I guess you’re right. Well, let’s just do the math. It’s ten and let’s just say I stay the next twelve hours. Twelve times one-hundred is twelve hundred bucks,” Dean smirked.

“Could you drive the car?”

Dean squinted in confusion, “What?”

The guy motioned to the car, “Can you drive the car? I own it but have no idea on how to actually drive it.”

The assassin chuckled, “So you bought a car and can’t even drive it?”

“Every car I’ve been in for the past ten years had my own personal driver. So, let’s just say my driving skills are rusty.”

Dean chuckled at the use of air quotes. “Yeah man, I could drive this car. Where am I driving it to?”

“Just get behind the wheel and I’ll give you directions.”

“Gonna need the key.”

The other man reached into his pocket and dropped it in Dean’s outstretched hand. He smirked as he walked to the car and unlocked it. The other man slid into the passenger seat.

“I’m Castiel by the way.”

“Got a last name?”

“Novak and what is your first and last name,” the guy said smartly.

The blonde grinned, “Dean Winchester sweetheart.”

Fifteen minutes later Dean pulled up outside one of the fanciest hotels he had ever seen. As soon as the car came to a stop, a valet was at the door asking if he could be of assistance. “Please park my cark in the reserved lot. I have a spot there, Castiel Novak.”

The girl’s eyes went wide, “Oh Mr. Novak, absolutely. I would be happy to sir.”

Cas slid from the car and Dean followed. Cas walked through the doors as if he owned the place, hell he might, Dean thought.

“Mr. Novak, hello. Is there anything you will be needing tonight,” a hotel employee walked up and asked.

“Yes, could you please send up a bottle of champagne and a bowl of strawberries to the penthouse suite,” Cas asked charmingly.

“Yes sir, absolutely. I’ll get it personally.”

“Thank you very much.”

Dean watched as the guy hurried off to fulfill his duty. Cas walked towards the elevator and the assassin followed. Thirty-seven floors later and the doors opened to a small lobby with a single gold door directly across from the elevator. Cas sauntered up to the door and pulled out his key card. The light on the handle turned green and the raven opened the door wide, motioning for Dean to enter.

The assassin stopped dead in his tracks, “Holy shit dude, this is like your own personal house. I mean seriously, I live above a bar and this one room is bigger than the entire bottom floor of the Roadhouse.”

The entire far side of the suite was nothing but sliding glass doors that lead onto a balcony. In front of one set of doors was a white Grand Piano. To the left was a loveseat, side table, and an ottoman to prop your feet up on. Further to the left was an archway and beyond that a dining room table with eight chairs situated around it. Dean turned to his right and gasped. There was a huge big screen TV with a couch, another loveseat, a recliner, and a large table placed in the middle. Beyond was a large sliding door which Dean guessed lead to the bed and a bathroom.

He was brought from his observations when he heard a chuckle behind him. He turned to see the raven with his head tilted, his shoulders shaking as he tried to contain his laughter now that he realized Dean was looking at him.

“I’m sorry for laughing but your expression is comical. You look like a child who has entered a toy store for the first time and realized how many different kinds of toys there are,” the man explained as he walked to a chair and laid his suit jacket across the back.

Before Dean could reply, there was a knock on the door. The blonde walked over to open it. The guy from earlier walked through rolling a cart. He stopped at one of the side tables and set a bucket of champagne on it. He also placed two glasses and a bowl of strawberries next to it before turning to Cas.

“Your champagne and berries sir. Is there anything else I can get you for the night?”

Cas smiled before waving his hand, dismissing the man, “No, that will be all, thank you.”

The guy looked at Dean expectantly. Dean stared at the man utterly confused as to what he expected. The other dude didn’t move.

The assassin turned to the raven, “Ugh, Cas, this guy isn’t leaving.”

The older man got up and pulled his wallet out of his pocket. He pulled a hundred from it and handed it to the hotel employee.

The man bowed his head as he said, “Thank you sir,” before turning around and heading out the suite.

Cas walked over to the bucket and pulled the bottle out. He opened it and poured a glass before handing it to Dean. He grabbed the strawberries before taking a seat on the couch. He motioned for the blonde to join him. Dean set the glass down so he could take his jacket off before walking towards Cas.

Dean sat down and took a large gulp of the champagne. He frowned, not used to the taste.

Cas held a strawberry out to him, “Here, take a bite of this.”

The assassin cocked an eyebrow, “Why?”

The raven smiled, “It helps to bring out the flavor of the champagne. Just try it.”

Dean smiled seductively before leaning over and taking a bite of the strawberry that the man held between his fingers. As the blonde bit into the fruit, flavors danced on his tongue. The other man had been right, the wine did taste better with the strawberry. Dean chewed slowly before swallowing and licking the juice from his lips. He smiled as Cas watched the movement.

“Take another sip of the wine Dean,” the man said in a husky voice.

The assassin shivered as he did as he was told. Once he swallowed the liquid, he finished the rest of the berry the other man held. Dean took Cas’s fingers in his mouth and licked them clean before swallowing the berry.

Cas’ breathing deepened and Dean felt his cock harden in his pants. They continued their little game of Dean drinking and Cas feeding him until his glass was empty. The raven took his glass and set it on the table before turning to Dean and pulling him into his lap.

The two men stared at each other before Cas leaned in and tried to kiss the blonde. Dean pulled away at the last second so that the man kissed his cheek instead.

The raven pulled back, confusion in his eyes. “Sorry, no kissing on the mouth, too personal. I’ll do just about anything else though,” the younger man explained.

Cas ran his fingers slowly down the blonde’s jaw, “How disappointing as I would very much like to kiss you right now.”

“Yeah, well sorry. That’s not a rule I’m willing to break.”

The other man grinned, “It’s good to know even a hooker has standards.”

“I ain’t got much else,” Dean quipped.

Cas smirked, “After tonight, you will have twelve hundred dollars.”

The blonde shrugged, “That is true. So, you wanna get on with the fun stuff?”

Dean slid to the floor and reached out to unbutton the older man’s pants. He had the button undone and was pulling the zipper down when suddenly Cas grabbed his hands and forced them still.

“Slow down, malen'kiy, we have all night. I’m going to go take a shower. Why don’t you watch some TV while I’m gone?”

Dean tilted his head at the strange word as the man stood up and walked towards the closed door. He opened it up and headed inside. The assassin had been right about that being where the bed was located. He watched the other man open a drawer and pull out some pajamas before heading out of sight. The blonde waited until he heard the shower turn on before pulling his phone out.

He dialed Charlie and waited for her to pick up. “What do you want Dean? I already told you, I’m not helping you find a case.”

The blonde rolled his eyes, “I don’t need your help Red, I think I already found one.”

“WHAT? Who,” the woman asked surprised.

“His name is Castiel Novak. So, is he a possible target?”

Dean waited for Charlie to search Novak’s name in the HC database.

He heard a gasp before, “OMG Dean, you need to get out of there now!”

“What, why? If he’s a target Charlie, you know damn good and well if the man has a price on his head, I intend to collect,” Dean replied angrily.

“You don’t understand. This isn’t some run of the mill street thug Dean. This dude has ties, really big ties,” the redhead explained.

“Ties to who Charlie?”

“The Russian Mafia.”

The assassin’s eyes widened in shock, “Well that explains the weird word he said earlier. Red, if this dude is part of the mafia, then he has to have a hit on him from someone.”

He heard Charlie typing on her keyboard before saying, “Actually no. Castiel is the son of Mafia don Chuck Krushnik, one of the most well-known names in Russia. Chuck had five children, Michael, Lucifer, Gabriel, Castiel, and Anna. Castiel chose to leave when he was eighteen. Apparently, he was Chuck’s favorite and so he allowed it without cutting Cas off.”

“So, Cas left, and his father let him? You’re telling me that the son of the leader of the Russian Mafia is a completely innocent guy? There’s no way,” Dean said disbelievingly.

“Apparently Cas wanted out because he didn’t want to be a part of all the nefarious activity. He moved to America, went to college at Harvard, and became the CEO of his own company. He has kept away from all illegal and illicit activity. Up until two weeks ago,” Charlie said slowly.

“So, what happened?”

“His sister was coming to visit him. She never got the chance to as her body was discovered in a hotel room. On the wall, written in her blood was a Russian phrase. When translated, it means come home brother. The police immediately interrogated Castiel but he was let go when it was made clear he knew nothing about what happened and was distraught at the loss of his sister,” the redhead explained.

“Is there any word of his brothers coming to the US? When I saw Cas at the bar earlier, he was surrounded by two bodyguards and three other guys. If I had to take a guess, I’d say they were his siblings,” Dean replied.

He waited a few seconds for the tech genius to reply, “Yes. It says here that Castiel’s brothers arrived in the US three days ago. All of them were interrogated but they all had alibis considering they were still in Russia.”

“Maybe after I finish with Cas, I’ll hit up one of his brothers. I’m sure they were behind his sister being killed even if they hired a third party to do so,” the blonde speculated.

“Dammit, Dean, you need to get out of there. These guys have more resources than we could fathom. Hell, their moles have moles. There is no way you could make it out alive if you get involved. Look, I’ll find you a target if that what it takes to get you out of there,” the redhead begged.

“Red, I got twelve-hundred dollars riding on this deal. Cas wants me for the whole night and is willing to pay that much for me to stay. I promise I’ll leave tomorrow and won’t go after any of his brothers,” the blonde swore.

“You better, remember I can track your phone asshat. Be careful and you better check in tomorrow by noon, understand?”

“I got it. I promise to,” Dean replied softly.

“Bye handmaiden.”

The assassin smirked, “Bye my queen.”

Dean put his phone back in his pocket and turned the TV on right as he heard the shower turn off. He looked through what was on and settled on one of his favorite shows _Dr. Sexy MD._ He relaxed back into the couch and a minute later Cas walked out, a pair of silk pajama pants slung low on his hips. He wore no shirt and Dean couldn’t help but stare at the strong chest. He licked his lips as his eyes skimmed over strong shoulders, pert nipples, and chiseled abs. The start of a happy trail could be made out as it disappeared into the man’s pants.

Cas caught him looking and smirked, “Like what you see?”

Dean’s mouth had gone dry and he could only nod. The Russian walked over to the couch and sat down next to the blonde. He reached out and trailed his fingers down Dean’s cheek and jaw before resting them on the man’s lips. They locked eyes as the assassin slowly enveloped the fingers in his mouth. He licked and sucked the digits until they were pulled away.

Cas grabbed the remote and silenced the show. He turned back to the blonde and smiled. Dean got the cue and slid off the couch to his knees. The raven reached out and wrapped his palm around the back of the blonde’s neck. He pulled Dean forward and the man shuffled on his knees until he was directly in front of Cas sitting between his spread legs.

Dean slid his fingertips up the man’s legs admiring how smooth the fabric of his pajamas were. The blonde could only imagine how much the damn things cost. He continued to move his hands up until he could grip the waistband and pull the pants down. Cas lifted his hips so that Dean could remove them completely.

The raven’s cock was already half hard and a bead of precum glistened at the tip. The assassin leaned forward, and kitten licked at the slit. Cas’ hips jerked and the man moaned. Dean smiled before sliding his mouth further down. He felt the flesh harden as he sucked. He bobbed his head up and down before popping his mouth off. He reached up with his hand and pumped the firm flesh. He licked at the thick vein on the underside.

Cas’ hips jerked again, and he muttered something in Russian. Dean paid no mind and he engulfed his cock in his mouth again, going all the way to the base. He loved that he had no gag reflex which made deep throating a specialty of his. He relaxed his throat as Cas’ tip pushed further into his throat. He kept the position for a few seconds before pulling back up. He kept up a steady rhythm as he bobbed up and down the thick cock. Saliva was starting to drip out the corners of his mouth allowing for him to move easier.

Dean reached his other hand up and fondled the Russian’s testicles, rolling and squeezing them gently. All of a sudden, Cas buried his hands in the blonde locks. He held Dean’s head still as he started thrusting his hips. The assassin relaxed his throat letting the older man fuck his mouth. He got off on his partners taking charge and using him as they saw fit. Dean continued to roll the man’s balls and could feel them tightening in his hand.

Cas suddenly pulled his cock from Dean’s mouth. He held the blonde’s head back by his hair and pumped his cock with his other hand. In seconds thick ropes of cum were shooting out of his cock and landing on Dean’s face. Cas grunted and muttered curses under his breath as he continued to strip his cock, making sure to get every last drop of cum out. He finally dropped his hands and slumped back on the couch.

The blonde licked his lips, savoring the taste of the man’s cum. It was salty and bitter but not the worst he’d ever tasted. He used his fingers to wipe the rest off his forehead and cheeks before sucking his fingers into his mouth as his eyes locked with Cas’. Once his fingers were clean, Dean leaned forward and licked the man’s cock spotless as well.

In a raspy voice, “I want you to make yourself cum for me malen'kiy.”

Dean hurried to unzip his pants and pull out his own hardened flesh. He was already so close to the edge that it only took a few pumps before he was doubling over and spurting cum onto his hand and the floor. “Oh fuck, Cas, so damn good.” Dean stroked himself through his orgasm before falling forward and resting his head on Cas’ bare thigh.

The Russian ran his fingers through Dean’s short hair as both men basked in the afterglow of their orgasms. They stayed that way for minutes, enjoying the quiet of the room and each other’s presence. Dean finally pulled away. He grabbed a towel that was lying on the table to clean the cum off his hand and the drops that had landed on the floor. He threw the towel to the side before climbing up onto the couch. Cas immediately pulled him into his arms.

He started to run his fingers through Dean’s hair again as he spoke, “That was very good malen'kiy. I have not had an orgasm like that in a long time.”

The blonde smiled as he traced lazy patterns against the skin of the raven’s arm, “What does that mean?”

“What malen'kiy? At the assassin’s nod, “It means little one in Russian.”

Dean bent his head backwards to look at the man, “You don’t sound Russian.”

The older man sighed, “I was born in Russia to a Russian man, but my mother was American. She was around more than my father was and so I learned English first and Russian second. I moved to the United States when I was eighteen and rarely ever return home. I am thirty now and so have lost my accent. A few words slip through every now and again though.”

“Why did you leave home? That must have been hard to leave your family,” Dean commented casually.

“My mother died in a car crash when I was fifteen. My father was more involved with his, uh, work than he was his family. My three older brothers were more concerned with trying to follow in Father’s footsteps. I had no desire to be a part of his business and so I asked him for his blessing for me to leave and live my own life. He granted it and so I came here. The only one I ever really missed was my sister,” the Russian said, sadness creeping into his voice near the end.

Dean moved so that he could face the other man, “Missed as in past tense?”

Cas looked down and away, “My sister was killed two weeks ago.”

“I’m sorry Cas, I didn’t realize. You don’t have to say any more,” Dean replied with fake concern, although it wasn’t as fake as he would want it to be.

Cas shook himself, “You sure do ask a lot of questions. Are you interrogating me or something?”

The blonde shrugged, “Or something. Hey, you’ve got me here all night, figured might as well make a little small talk.”

“You are a strange person Dean, but I like people who are different. Come, let us go make more small talk in the bedroom.”

“Are we really gonna make small talk,” the blonde wiggled his eyebrows.

The other man smiled, “I’m sure we will sometime or another.”

Dean chuckled before following the man into the room. It turned out Cas was right. They did up making small talk, two hours later. They talked until they fell asleep.

The blonde woke slowly, more comfortable than he had been in ages. He rolled onto his stomach and wrapped his arm around the feather stuffed pillow. He kept his eyes closed, waking up slowly. When he was fully awake, he rose from the bed and stretched before walking out the room to find Cas. The Russian was sitting at the dining table surrounded by dozens of plates of food. He himself had a plate of pancakes covered with syrup.

Dean walked up and took a seat across from him. He could only gape at all the food in front of him. Some of it he could identify while some dishes he could only guess as to what was in them. He pulled a plate full of fried eggs and bacon towards him as well as a plate of pancakes.

Cas motioned at the spread, “I wasn’t sure what you liked so I took the liberty of ordering everything the menu had to offer.”

The blonde smiled, “Thanks. It all looks amazing but there is no way I’m gonna be able to eat it all.”

The other man shrugged, “Oh well. As long as you have something to eat, that is all that matters. Did you sleep well?”

Dean munched on a piece of bacon as he replied, “Yeah, like a damn baby. Best sleep in a while.”

Cas nodded, “Good, I am glad.”

Dean picked up another piece of bacon before asking, “Before I head out, can I take a shower?”

“Absolutely although I would recommend using the bath. The tub has built in jets and makes for a wonderful massage.”

“Definitely taking a bath then. Thanks for telling me.”

The raven smiled, “Of course Dean. If I leave while you are in there, I will put your money on the table next to the chair with your jacket on it.”

“Uh thanks. So, where you headed off to today,” the assassin asked casually.

“Believe it or not but I do have work to attend to. I have quite a few meetings today that I have to take care of,” the man replied nonchalantly.

Dean shoved a huge piece of pancake in his mouth and chewed for a moment before asking, “What kind of work you do?”

“I am the CEO of my own company.”

“What kind of company?”

“So curious. When I started out, I was raising my own bees and selling the honey they produced. Over time, I started making different flavored honeys and my simple business has turned into a multi-million-dollar corporation. We produce over one-hundred different types of honeys as well as jams, jellies, herbs, spices, amongst other things,” the older man explained.

“Wait a minute, you aren’t talking about Humble Bee are you,” the blonde asked incredulously.

“So, you have heard of my company then,” Cas replied, obviously amused.

“Heard of it, dude you guys make the best honey I’ve ever tried. Your habanero flavored honey is the bomb,” Dean remarked.

“That was definitely one I didn’t think would work but it has turned into one of our best sellers.”

“You ever quite producing it and I might just have to kill you,” the assassin quipped.

“I will be sure to never stop its production,” Cas joked.

“Good.”

Once Dean finished his food, he headed to the bathroom. Cas watched the man walk away, appreciating the sight. He wished Dean would stay longer, the younger man made for interesting but enjoyable company.

He phone started ringing and he pulled it out to see who was calling. “Hello Gabe.”

“Heya Cassie. So, what happened to you last night? Raphael and Gordon said you left the club and wouldn’t let them follow you.”

“Yes, well all of my brothers headed backstage for some fun and I didn’t feel like sitting around like the fourth wheel, so I left. Turns out, I ended up having my own fun,” he smiled as he thought of Dean.

“Oh, Cassie, what crazy stuff did you get up to last night?”

“I ended up bringing a hooker back with me. We had a very enjoyable night.”

“Cas, are you serious,” the man barked out angrily.

The raven frowned, “Do not get mad at me when you disappeared with three women Gabriel.”

“Yeah but I know those three. What if this dude is the same one who killed Anna? He could be an assassin sent to kill you,” the short man replied furiously.

Cas chuckled, “Dean is not an assassin sent to kill me Gabriel. He is a hooker and was looking to make some money. I brought him home and we fucked. End of story.”

He heard his brother let out a huff, “Whatever. Do you have a plan on how we are going to figure out which of our brothers had Anna killed?”

“We need someone who they will talk around but who can spy for us. You know our brothers can’t keep their mouths shut.”

“Agreed. Everyone I know, both Lucifer and Michael would recognize. You got anybody?”

Cas got up and started pacing. He walked towards the bedroom without thinking and heard singing. He walked through the room and into the bathroom. Dean was in the tub, completely covered in bubbles and was rocking out. He had earphones in and was singing Led Zeppelin’s _Stairway to Heaven._ The Russian smiled at the carefree attitude the younger man was exhibiting.

“You know Gabe, I might have an idea. Let me talk to him and I will let you know.”

“You’re talking about the hooker, aren’t you?”

“Michael and Lucifer have never met him and something about Dean tells me he would be good at spying on people,” Cas replied defensively.

“Whatever, just make sure he is dressed appropriately. Don’t forget the dinner we have planned tomorrow with our brothers.”

“I haven’t Gabe. Now, I need to be going, I have a business meeting in a little bit.”

“Bye bro.”

“Goodbye Gabe.”

The phone call dropped, and Cas slid his phone back into his pocket. He sat on the edge of the tub and continued to watch Dean. The man actually had a very pleasant voice and Cas wouldn’t mind if he got to listen to it again.

Dean opened his eyes and froze at realizing he was being watched. He pulled an earbud out, “Gotta love Zeppelin.”

The raven smiled, “Yes and such an iconic song.”

“Yeah true that. Uh, is there any reason you are watching me,” the man asked nervously.

“Dean, I have a proposition for you.”

“What kind of proposition?”

“I’d like to hire you for the week to be my own personal escort.”

Dean sat up quickly, shock evident on his face. “What?”

“My brothers are in town and I have a lot of meetings with them this week. I need to bring a plus one with me and I figured you could be it for me. I also need your assistance with something else.”

“What kind of assistance,” the blonde asked skeptically.

“Well, I told you my sister was killed recently. I believe one of my brothers had her killed to try and get me to go back home. My father recently announced he will be retiring and as of right now, he wants to leave the family business to me. I have no desire to run it and have made it very clear. I think one of my brothers had Anna killed as a threat to me. I want to know which one did it and I was hoping you would help spy for me and figure out who killed her,” the Russian explained.

Dean faked shock at the fact that someone would kill another person as a threat, “Oh my God, Cas that is awful. Don’t you think you should go to the police or something? I can’t believe they would kill their own sister!”

“They never cared about Anna because she was only their half-sister. Our mother was kidnapped, and Anna was the product of that kidnapping. Father was never mad at my mother or Anna, but my mother was different after that. My brothers blamed Anna and so never had much to do with her. Anyways, the police have already dismissed my brothers because of their alibis. I’m sure one of them hired someone to kill Anna and I want to know who. Will you help me or not Dean,” the man asked sternly.

Dean could barely contain his eagerness at the job that had just landed in his lap. He had every intention of helping Cas, but he had to play the part of scared civilian. “Cas, I, uh, don’t know. I mean not to be rude but I kind of like living. I’m not ready to die yet.”

“Dean, I promise you that no harm will come to you. You’re going to be my pretty arm candy. Act a little ditzy and my brothers will dismiss you completely. My brother Gabe and I can’t do this on our own, we need some help. I promise to pay you handsomely,” the Russian said with a smirk.

The blonde cocked an eyebrow, “How much we talking about here Cas?”

Cas thought a moment before replying, “Well, my brothers leave in a week so I would need your assistance for that time frame. So, twenty-four hours a day times one-hundred is twenty-four hundred. Multiply that by seven and you get, um let me see, sixteen-thousand-eight hundred. If you help me figure out which brother had Anna killed, I’ll make it an even twenty thousand. Does that sound like a fair price?”

Dean wasn’t acting as his jaw dropped in shock. “Twenty thousand dollars,” he asked incredulously.

Cas nodded. “Only if you help me figure out the brother who killed Anna but you’re guaranteed the sixteen-thousand-eight hundred no matter what. So, do we have a deal Dean?”

“Yeah, Cas, we have a deal,” the assassin nearly shouted. In his excitement, Dean slipped and fell into the water. He quickly sat back up and spit water out his mouth.

“Finish your bath. We will talk more before I leave for work,” Cas said as he got up and walked out the bathroom.

Fifteen minutes later and Dean, wrapped in a fluffy robe, settled in a chair at the dining room table where Cas was working on his laptop. The raven closed the laptop when he realized Dean had joined him.

“Hey Cas,” Dean said, unsure of what to say.

The man smiled, “Hello Dean. I have to leave for work in a few minutes. I have a dinner party with my brothers tonight. I can’t have you showing up in what you had on last night. I’ll leave some money so you can go shopping to get some clothes for tonight.”

“We talking suit and tie or what Cas?”

“No, you won’t need a suit, but a nice pair of dress pants and shirt will be required. Also, a pair of shoes that aren’t boots. Something like how a golfer would dress,” the man explained.

Dean grimaced, “Not really my style but hey, you’re paying me, so I’ll wear a dress if you asked me to. You aren’t gonna ask me to wear a dress, are you?”

The raven chuckled, “No, at least not in public but here in this suite, I think you would look good in a dress.”

“Keep dreaming man, I ain’t wearing a dress. Lingerie maybe but no dress,” the blonde admitted with a blush.

“I shall keep that interesting tidbit in mind. Here is five thousand dollars. Be ready and meet me at the lobby bar by a quarter to six,” the Russian said as he pulled money from his wallet. He set it on the table before grabbing his suit jacket and slipping it on.

Dean grabbed the money and turned to look at the other man, “You know Cas, I’m gonna treat you so good you aren’t gonna want let me go.”

Cas smirked, “One week Dean, and I will let you go. A quarter to six; don’t be late.” The assassin chuckled as the other man left the room.

As soon as the door shut, Dean called Charlie. “You had five minutes before I was about to call in the police on you,” the redhead threatened.

“Yeah, yeah, retract the claws Red. Look, I have a dinner party I’m going to tonight and Cas gave me some money to go buy clothes. Where the hell do I do that,” Dean asked, slightly panicking.

“Seriously, that’s what you’re gonna ask me right now?”

“I’ll fill you in later but first where do I get clothes?”

“In Beverly Hills?”

“Yeah!”

“Rodeo Drive baby.”

“Thanks Charlie, I promise to call you later. I gotta go,” Dean said not even giving the woman a chance to say goodbye.

Dean hurried into the bathroom to brush his teeth and style his hair. He didn’t have any clothes except for the ones from the night before so he brushed them off and got dressed. He donned his jacket and shoved the money into his wallet before heading out.

He headed into the lobby and tried not to care about all the people staring at him. He knew he stuck out like a sore thumb with his holey jeans and worn leather jacket. Every person he saw had fancy designer clothes with perfectly manicured nails and wonderfully styled hair. Dean straightened his back, relaxed his shoulders, and held his head up high trying to not give a care in the world.

As soon as he was outside, he let out a breath of air. He grabbed his phone to try and figure out just how far Rodeo Drive was. It was a short fifteen-minute walk and he headed in the direction the map told him to go. When Dean stepped foot on the right road, he stopped in stunned silence. The road was full of some of the most luxury stores he could have ever imagined. Names such as _Giorgio Armani, Gucci_ , and _Louis Vuitton_ were just a few that stuck out. Dean gulped, never having been so out of his element before.

He walked down the street feeling completely inadequate. The people here were more dressed up than at the hotel and he didn’t think that was possible. As he walked, almost everybody stopped and stared at him. He wrapped his jacket tighter around himself as he finally stepped into a store, not even looking to see what it was called.

The bell above the door jingled as the assassin walked through. He saw a rack of polo shirts and headed towards them. He picked one up and had to admit the material felt amazing against his skin. He looked at the price tag and nearly puked, three hundred dollars for a single shirt. He quickly folded it up and put it back on the shelf.

He heard a small cough behind him and spun around. There was a man standing there in some of the finest pants and shirt Dean had ever seen. The man was scowling as he looked Dean up and down. Dean chewed on his lip knowing the man wasn’t impressed with his look. Hell, his whole outfit had cost a fraction of just the one shirt.

“May I help you sir,” the man asked with an irritated and nasally voice.

The blonde rubbed at the back of his neck nervously, “Uh, yeah, see I need to buy some clothes for a dinner party I’m going to later.”

Another sales associate walked up, her high heels clacking against the linoleum floor. She gave him an even more disgusted look than the male associate.

“Amanda, do you think we have anything in our store that he would be able to afford,” the man asked haughtily.

She rolled her eyes before replying, “No Brad, I don’t think there is. Our store carries nothing but the finest men’s clothing. From what I can see, this man shops in the discount section of a _Goodwill._ ”

The man chuckled before turning back to Dean, “See, sir. There is nothing here that you could ever hope to afford so I’m going to ask you to leave.”

The assassin’s neck and face were flushed red from embarrassment. He couldn’t even feel mad because the woman was right. He might work for the government, but they didn’t pay all that well and besides Dean figured why spend more for clothes when the cheap ones were just as good.

“Look, I have money, I can pay,” he tried to explain.

The woman cut him off, “We said get out. Now, if you don’t remove yourself from the premises, I will call the cops and have you escorted out in handcuffs.”

Dean glared at the two associates but hurried out the store regardless. He couldn’t help the few tears that were falling down his cheek as he walked back to the hotel. He hugged his jacket as close to his body as possible, the cash in his pocket a heavy weight.


	2. The Plan

**Summary for the Chapter:**

> Dean finds some unexpected help from a new friend. He and Cas go to the dinner party with Cas' brothers which turns out to be a boring affair. Cas and Dean enjoy a day of shopping together. Cas helps Dean face his past. Lots of smut throughout.

**Notes for the Chapter:**

> Here is the second chapter, hope you guys enjoy it. So, I've tried to include as many of my favorite moments from Pretty Woman as possible but also keep it to the nature of the story.

He slipped back into the hotel and headed for the elevator when a hand grabbed his elbow and forced him to stop. He turned around to see a tall red headed woman glaring at him.

“Hello, my name is Rowena MacLeod and I’m the hotel manager. Now, sir, can I ask what you are doing in my establishment,” the woman asked, her Scottish accent heavy.

Dean jerked his elbow away from the woman and threw his hands up in the air, “Look lady, I’m just trying to get back to the suite that the guy I’m staying with is in.”

“And what is the name of the guy you’re staying with?”

“It’s uh Cas-teel uh Cas-tile,” Dean was so frustrated he couldn’t even remember Cas’ name. He looked up and saw the employee from last night, “Hey, that guy knows me. He brought strawberries and champagne up to the room last night. He’ll vouch for me.”

Rowena snapped her fingers and motioned for the man to come over. “Kevin, is it true you recognize this man?”

The black-haired boy shook his head nervously, “Yes ma’am, he is staying with Mr. Novak in the pent-house suite.”

The manager smiled, “Thank you Kevin. You are dismissed.”

The boy nodded before scurrying away. The woman turned back to Dean.

“Sir, Mr. Novak is one of our most special guests and so we allow him a few luxuries we wouldn’t allow others. Now follow me,” she said as she turned on her heel and walked away.

“Great, now where are we going,” Dean snapped as he followed.

She said nothing as she held a door open and motioned him inside the office. She pointed to one of the plush chairs while she went and took a seat behind her desk. Dean slumped into the chair heavily.

“Now, Mr. uh?”

“Winchester. Dean Winchester,” the man replied listlessly.

She smiled, “Ah yes, Mr. Winchester, as I was saying Mr. Novak is a very special guest but even with that being said, this hotel has certain standards. One of them being that all of our guests dress with a certain degree of decorum you could say.

Dean reached into his wallet and pulled out some of the bills Cas had left him and dropped them on the desk in front of him, “Well, I tried to go get clothes today for a dinner party tonight but the store employees wouldn’t help me. They turned me out before I could even try and explain. So, I’m sorry if I don’t look prim and proper enough for you.”

Rowena stayed silent as she picked up the phone and started dialing someone.

“Oh great, just call the cops on me why don’t you,” Dean yelled.

Rowena smiled as she replied to the person on the phone, “Hello, this is Rowena Macleod, hotel manager of _Beverly Hill’s Hotel and Resort._ Can you patch me on down to Crowley in men’s clothing please? Thank you, and you have a great day as well.” After a moment, “Hello Fergus, it’s Mommy. I have a friend here in front of me, a Mr. Winchester who is the, uh, nephew to a very important guest, Mr. Novak. Mr. Winchester needs to buy some clothes and I would appreciate it if you could be a dear and help him.” There was another pause before she replied, “Thank you Fergus. He shall be there in ten.”

Rowena hung the phone up before smiling at Dean, “There you go. I’ll have Benny drive you over.”

Dean stared in shock before replying, “Thank you. I don’t know how to repay you.”

“Promise me, when Mr. Novak leaves at the end of the week, that this will be the last time you or I ever see one another. Understood?”

Dean nodded, “Understood.”

Rowena pulled out some papers, clearly dismissing the young man. Dean hurried out his seat and walked back out the hotel. There was a burly limo driver waiting outside. He introduced himself as Benny before ushering the blonde into the car.

Ten minutes later and Dean was walking into another clothing store, nervous, unable to shake the memories from his last shopping attempt.

A short man in a well-tailored suit walked up to him immediately, “Are you Mr. Winchester. I’m Crowley, my mother sent you over.”

Dean gave a small smile as he shook the man’s offered hand, “Yeah, that’s me.”

“Well, follow me, I will have you leaving here with the best clothes you’ve ever worn. Your pant size is a thirty-four waist and thirty-two length, and you wear a large size shirt,” the man asked as they headed upstairs.

Dean was impressed as he followed, “Woah, yeah spot on. You’re good.”

Crowley grinned, “Well, when you’ve been doing this as long as I have, you pick up a thing or two. Now, let’s find you something that your uncle would approve of.”

“Hey, Crowley, you know Cas isn’t my uncle.”

“They never are my boy.”

An hour later and Dean was walking back into the hotel, a garment bad slung over his shoulder. He hurried up to the suite and as he walked in, he heard the phone ringing. He dropped the bag over a chair and rushed to pick the phone up.

“Hello.”

“Never pick the phone up if I’m not there Dean,” Cas reprimanded.

“Then why you calling in the first place,” the blonde chided.

“I was just checking up on you.”

“Well, I got some clothes for tonight,” Dean smiled as he replied.

“Very good.”

“Where we meeting with your brothers anyways,” the assassin asked.

“We are gathering at my brother Gabe’s mansion. Remember to meet me in the lobby at a.”

Dean cut him off, “A quarter to six, I know.”

“Goodbye Dean.”

“Bye Cas,” the blonde hung up. A moment later the phone rung again, “Hello.”

“I told you not to pick it up.”

“Then quit calling me man,” Dean chuckled. He heard a soft laugh over the phone before hanging up.

He pulled his phone out and dialed Charlie, “Hey, Red, what’s up?”

“Nothing much. You gonna fill me in on everything now?”

Dean spent the next twenty minutes telling Charlie everything that had happened over the last day and a half.

“Get this, he gave me five thousand dollars to go get clothes tonight for some fancy dinner party at his brother’s mansion. Can you believe that,” Dean nearly shouted.

“The only thing I wanna believe is you trying to eat with those fancy table settings. Hell, ninety percent of what you eat, you use your hands for,” the redhead remarked.

Dean bolted upright, “Oh shit Charlie, you’re right. I gotta go.”

He hung up before she could reply and hurried down to the lobby. He searched for Rowena and made a b-line straight towards her.

She heard him approaching and turned to meet him, “Mr. Winchester. How pleasant to see you again.”

“Hey, I got some clothes for tonight so thinks for that. I kind of need your help again,” Dean rubbed at the back of his neck nervously.

“What can I assist you with now?”

“I have no idea what any of those fancy plate settings mean,” the blonde admitted softly.

Rowena smiled before grabbing his hand and pulling him along. Dean stumbled along behind her until she stopped by a table in the dining room. She pulled a seat out and forced Dean to sit down. There was a complete place setting in front of him and he grimaced at all the silverware in front of him.

“Ok Dean, to the left of the dinner plate, the large fork in the center is the dinner fork. It’s the biggest fork so that should be easy to remember. The fork to the left is the fish fork and the fork to the right is the salad fork. Remember, you use the forks in the order they are set,” the manager explained.

Dean nodded his head, “Ok, so that should be easy enough. The big fork is the dinner fork and just use the forks in order. So why are there two knives?”

Rowena pointed to the silverware to the right of the plate, “The larger one is the dinner knife and the smaller one is the fish knife.”

“Wait, why doesn’t the fish knife go first if the fish fork went first,” the blonde asked exasperated.

“That’s just the way it is deary. Now, next to the fish knife is the soup spoon and next to that is the oyster fork,” the redhead continued to explain.

“So, why doesn’t that fork go with the other forks? When do I use that fork?”

“Only if shellfish are served. Now you see the small plate and the knife on top of it,” the manager asked.

“Yeah, what is that, the stuff for dessert?”

“Nope, that is the butter plate and the butter knife.”

“So, butter gets its own plate and knife. Ok. Why are there so many glasses, how much am I expected to drink,” the blonde whined.

“So, the big goblet directly above the knives is the water goblet. Next to that you will have either a red or white wine glass. The last glass is the champagne glass. And to top it all off, the napkin sits in the center of the dinner plate. So, you got it all,” she asked expectantly.

“Uh, the big fork is the dinner fork and we use the forks in the order that we eat, oh, and butter gets its own knife and plate. That’s about it,” the blonde replied.

Rowena shook her head before starting to explain everything all over again. Dean groaned, there was no way he was going to get all of this. After an hour, he definitely knew the forks and the butter plate and knife. The other stuff was still kind of hazy. He didn’t have any more time because he had to go get dressed.

Cas walked into the hotel lobby looking for his plus one. His eyes scanned the bar but none of the patrons could possibly be Dean. He continued to scan the room when movement at the bar caught his eye. A tall man turned around and Cas barely managed to not gasp aloud. The man getting up and walking towards him was none other than Dean. He was dressed in a pair of tan pants and an ocean blue polo that brought his eyes out beautifully. Cas checked his shoes and was glad to see a pair of black loafers on his feet. Dean had even styled his hair, so it was artistically slicked back and showed off his eyes even more.

The young man walked up, a small smile on his face, “How do I look?”

Cas smiled brightly, “You look amazing! Shall we depart?”

The Russian held his arm out and Dean wrapped his own around Cas’, “Let’s go.”

The two men walked out, and a few heads turned at the handsome pair. Cas had left his suit jacket and tie behind but was otherwise dressed in his work attire, tan pants and a dark purple long-sleeved dress shirt. Once outside, Cas headed to a limo that was parked outside. The driver held the door open as they approached. Cas was the first to slide in and then Dean was right behind him.

They rode in silence and arrived outside a large mansion after half an hour. Dean stared wide eyed at the building. In his wildest dreams, he never thought he would step foot inside such a large and extravagant place. He gulped audibly but tried to play it cool.

Cas leaned over and whispered in his ear, “Just relax, you’ll be fine.”

Once they were out the car and started walking up towards the front door, Castiel started to explain, “Gabriel acts like an overgrown child and will absolutely love you. My other two brothers are so snobbish that they will likely be engaged with each other all night. So, it should be easy for you to slink around and listen in on them. Here is the recorder, I want you to record every single thing you hear them say. Understand?”

Dean grabbed the recorder from Cas and tucked it into his pocket. “Got it, record everything and act inconspicuous so they pay me no mind. Wont they notice you bringing some stranger to the party though?”

“We all bring a different guest every time we attend these things, so hardly. Unlike my brothers, my guests are simply guests. You will be the first one that I’ve brought who I intend to fuck afterwards,” the Russian said in a low voice.

Dean blushed but didn’t have a chance to respond as the door was opened and they were let in. He didn’t get to take much in as they were led to a large dining room. It seemed they were the last to arrive. Dean recognized no one except for Cas’ three brothers. One was sitting at the head of the table, four women hanging all around him. He had one on each arm of the chair, one in his lap, and one behind him, her arms wound around his throat. Every woman was dressed in a sparkly cocktail dress of varying colors.

By the window, the other two brothers stood close together, their voices soft as they talked to one another. Going off what Cas said, the one at the table was Gabriel and the other two were Lucifer and Michael. Dean looked around and saw a few other people sitting or standing around. He figured they must be Lucifer’s and Michaels dates.

No one looked up as they walked in and Cas led him to a secluded corner. “The one at the head of the table is Gabriel. You will always see him with at least two women hanging of his arms. He is quite fond of orgies. Michael is the tall brother with the dark brown hair. If I had to guess, the couple standing over there in the other corner are his guests. He has a thing for sleeping with couples. The blonde next to him is Lucifer. The young man over there who looks like he wants to bolt is most likely his guest. My brother is sadistic and loves to break young twinks in as he puts it.”

Dean scowled at the tall blonde, “You ever think he might be the one to kill your sister?”

Cas sighed, “He is the number one suspect on my list, but I need the proof before I take care of him. That’s where you come in.”

Before Dean could reply, a butler walked in and announced, “Dinner is served.”

Everybody took their seat. The women around Gabe took the chairs closest to him. Cas and Dean sat to his left after the women. Michael and his guests sat to the right of Gabe after the women. Lucifer and his guest were at the end of the table.

“Cssie, I didn’t even realize you had arrived. Who is the scrumptious eye candy next to you,” Gabe asked with a flirtatious eye wiggle.

“This is my guest, Dean. I see you found quite an entourage brother,” Cas commented as a plate of shellfish was set in front of everyone.

Dean blanched, he forgot which one was the fork for shellfish. He started to reach for one fork before dropping his hand. He then reached for another but dropped his hand again.

He leaned closer to Cas and whispered, “Which fork is for shellfish? I know the dinner fork and that’s about it.”

Gabe spoke up, “Don’t feel bad Dean-o, I could never figure out this fancy table setting stuff. Use whatever fork you want, it’s a judge free zone.”

The assassin smiled before picking up a fork and trying the oysters in front of him. They were too slimy for his taste and only ate one. The rest of dinner went off without a hitch. They had a five-course meal of oysters, fruit, salad, the entrée, and dessert. By the end of it, Dean was so full, he couldn’t take another bite. Throughout the meal, Gabe spoke mostly to Cas and Dean. He tried to engage Michael and Lucifer, but they gave clipped responses, so Gabe gave up.

Once dinner was done, they stood up and headed to a chamber room. Gabe immediately sat on the couch and his group of women followed. Michael and Lucifer went to a corner and started talking. Their guests sat in the chairs scattered around. Cas joined his brother and motioned for Dean to go spy on his brothers.

Dean grabbed a glass of wine and sauntered towards the brothers. There was a large plant near them that Dean was able to stand behind without the two men noticing him. He took the recorder out his pocket and turned it on. He set it on top of the soil, making sure it was hidden from view before walking away.

He joined Cas on the couch. The man looked at him confused, “What are you doing?”

Dean leaned closer to the man to make sure their conversation couldn’t be heard, “Don’t worry, I left the recorder in that plant over there. I didn’t want them to catch me. Trust me, they will never spot it. I’ll go back over there in a few minutes.”

The blonde kept true to his word, he went back towards the plant and noticed the two men were still deep in discussion. They were speaking in Russian and Dean didn’t understand any of it except for two words, Anna and Castiel. Dean froze, but the men said a few last words before moving away from each other.

Michael turned towards Dean and scowled at seeing him, “What are you doing?”

The assassin stood up quickly, “Cas asked me to come and get you. He needed to talk to you about something.”

The man stared at him before walking off. Dean gave a sigh of relief before grabbing the recorder and tucking it back into his pocket. He saw Lucifer and the young boy walk out the room. Michael and Cas were talking as he headed towards them.

As soon as he arrived, Michael stood up and left. Dean watched as he walked towards the couple and they all left together. He turned back to Cas and quirked an eyebrow in question.

Cas rubbed at his forehead in frustration, “Michael is upset that I haven’t figured out who killed Anna yet.”

“I thought you said he didn’t care about her,” Dean commented.

“I didn’t think he did but maybe I was wrong. Are you ready to go?”

“Yeah, I’ve had enough of this place.” He looked around for Gabe but found the other man had already left.

“If you’re searching for our host, I’m afraid he was the first to leave. Like I said, Gabe lives a very flamboyant life. Dad was very happy when he left Russia and wanted nothing to do with the business either,” the older man explained as they headed back to the limo.

“So, is every family affair like this? I mean this was, honestly it was awful. Gabe was caught up in the women, and Michael and Lucifer only wanted to talk to each other,” Dean remarked as they drove back to the hotel.

“Yes, believe it or not, this was one of the better family gatherings. Normally, it turns into some kind of screaming match between my brothers,” Cas sighed as they pulled up to the hotel.

They headed inside and went straight to the suite. Cas grabbed a bottle of wine out the fridge and opened it. Dean opened the door to the balcony and looked outside. The view was breathtaking, and he soaked up the breeze that was blowing. Much better than the stifling atmosphere he had been in for the past few hours.

Cas joined him and handed him a glass. They drank together in peace. Once both glasses were empty, Cas grabbed Dean’s hand and headed back inside. They set the glasses on a table before heading into the bedroom.

Cas’ hands immediately went to the waistband of Dean’s pants. He unbuckled the belt and slid it through the loops before dropping it to the ground. He unbuttoned the pants and let them pool around the man’s feet. He slipped his fingers into the boxers the blonde wore and forced them down his hips and let them drop to the floor.

He grabbed the hem of Dean’s shirt and pulled it off, dropping it on the floor. He then pushed the blonde backwards until he toppled onto the bed. He leaned over and kissed along the man’s jaw as his fingertips ran up and down Dean’s body causing the man’s skin to erupt in goosebumps.

He pulled away and in a husky voice, “You are absolutely stunning malen'kiy. I am going to enjoy fucking you.”

Dean looked up, lust evident in his eyes, “You gotta get naked if you’re gonna fuck me.”

The blonde had never seen someone shed his clothes so fast before. He watched as Cas went to a bag that was sitting on the floor. He pulled a bottle of lube and a condom out. He threw them on the bed as he joined Dean.

Cas moved until his mouth hovered over Dean’s dick and completely engulfed the hardened member in one move. The assassin’s back bowed as he shouted out in pleasure and shock. Cas set a fast pace as he sucked on the dick in his mouth. He grabbed the lube bottle and squirted some on his fingers before shoving one roughly into Dean.

The man grunted at the slight burn, but it wasn’t anything he couldn’t take. He slowly started thrusting his hips as Cas blew him. “Gah, Cas, yeah just like that, buddy. God your mouth feels so fucking good!”

The Russian responded by thrusting another finger inside Dean’s slick hole. He started scissoring his fingers, trying to stretch the tight ring of muscle as quickly as possible. As soon as he could easily move his fingers, he thrust a third finger inside of the willing body beneath him.

Dean moaned, “Enough, I’m good, fucking fuck me already!”

Cas popped his mouth off Dean and grabbed the condom packet. He ripped it open and quickly rolled the rubber onto his hardened flesh. He used some of the extra lube around Dean’s hole to slick his cock up. He pulled the other man towards him until their hips were flushed. He threw Dean’s legs onto his shoulder before plunging inside of the man.

The blonde screamed; he wasn’t stretched quite enough for Cas’ large girth but truthfully, he loved the stinging pain. He snaked his hand down and wrapped it around his dick. He started pumping in time with Cas’ wild thrusts. The Russian had set a brutal pace. He leaned over even more and that gave him a better angle, allowing him to plow into Dean’s prostate.

“God, Cas, right there! Right fucking there man, so fucking close,” Dean shouted as pleasure coursed through his body.

With one more hard thrust, Dean’s cock erupted, spewing cum over his hand and stomach. He flopped bonelessly against the bed as Cas continued to fuck him. Cas was panting hard and his thrusts were becoming erratic, signaling he was close. With a grunt and a muttered, “Fuck,” Dean felt Cas’ cock pulse inside his body. With a last few shallow thrusts, Cas dropped onto the blonde heavily. Dean grunted at the sudden weight but made no move to shove the Russian off him.

They both lay there panting hard, waiting for their heartrates to return to normal. With a groan, Cas’ soft cock slipped out of Dean’s body. He rolled over and pulled the condom off. He tied it before standing up and heading to the bathroom. He came back with a washcloth and quickly wiped off Dean. He dropped the rag before crawling back into bed.

The blonde smiled when the other man scooted until his chest was flush with Dean’s back. Cas threw an arm over his waist and pulled him back. He placed a tender kiss behind the blonde’s ear and muttered a quick, “Goodnight Dean,” before falling asleep.

Sleep did not come so easily for the assassin. He sighed deeply knowing what was happening, something that wasn’t supposed to. He was starting to develop feelings for the man behind him and that wasn’t allowed. One of Dean’s rules was to never catch feelings for a target. But Cas wasn’t a target. He also thought Dean was a hooker and once he learned the truth, he’d never want to speak to the blonde again. The assassin eventually fell into a troubled sleep.

The blonde woke up late the next morning to an empty bed. He stretched and slipped a robe on before heading out the bedroom. Cas sat at the dining room table, a cup of coffee in his hand as he listened to the recording. When he looked up and saw Dean approaching, he turned it off.

Dean grabbed a cup of coffee before having a seat. He motioned to the recording, “Don’t stop on my account. They were speaking in Russian and I don’t understand a word of what they said except they mentioned your name and Anna’s.”

Cas nodded, “Yes, they were talking about who killed her. They wonder if her death will be enough to get me to go back home and take over Father’s business. Both of them want to take over and they started arguing over who would be able to run it better.”

“Did either slip up and outright say, they killed her?”

“No, they aren’t that foolish,” the man replied as he picked the recorder up and erased everything Dean had gotten the previous night.

“So, is her death enough to get you to go back?”

“No, I have no intention of ever following in my father’s footsteps. I have everything I ever wanted here in America. I just want to figure out which of my bastard brothers had my sister killed,” the Russian growled.

Dean reached out and put a hand on Cas’ arm, “We’ll figure it out Cas, I promise. We still got six days together.”

“Thank you malen'kiy, you are right.”

“Of course I am, so what’s on the agenda today,” Dean asked with a smile.

“Work I suppose. Thankfully, the next gathering with my brothers isn’t until tomorrow.”

“I’ll have to go buy more clothes then, huh,” Dean questioned despondently.

The raven cocked his head, “Yes, why didn’t you buy more clothes yesterday. I know the outfit you wore last night didn’t cost five-thousand.”

The blonde shook his head but refused to meet the other man’s eyes, “It wasn’t but I really don’t wanna have to go shopping again.”

“Why not?” Dean shrugged without answering. “Dean look at me.” Cas waited until he did so before continuing, “What happened?”

The other man huffed before replying, “The salespeople were rude to me. Completely dismissed me because I wasn’t wearing fancy enough clothes.”

Cas pulled his phone out, “Gabe, I won’t be making it into work today. I’ve had something come up that I need to take care of. Yes, I will still be meeting up with our brothers tomorrow.”

Dean looked up, “Why did you call out?”

The Russian smiled brightly, “Because you need more clothes and I refuse to let you be mistreated again.”

The blonde was shocked, “You didn’t have to do that. I would have been ok.”

“It’s done Dean. Now, you look to be the same size as me so you should be able to wear some of my clothes when we go out today. Did you want any breakfast or are you ready to head out,” Cas asked with a self-satisfied smirk on his face.

“Let’s just get this over with,” the blonde grumbled.

Half an hour later found Cas in a seat watching Dean being surrounded by store employees offering him clothes of every different color, fabric, and designer. The man seemed overwhelmed as item after item was thrust into his face. He looked at the Russian, pleading with his eyes to help him.

Cas raised a hand and everybody immediately quieted, “Alright, Dean needs enough day outfits for one week. Casual clothes and simple fabrics, nothing too clingy or itchy, preferably in darker colors to bring out his gorgeous eyes. We will also need two nights worth of suits as well as some fancier clothes for evenings out but do not require something as upscale as a suit. Basic necessities such as socks, ties, and undergarments are also required along with a couple pair of shoes. Dean, is there anything you would like special?”

The man chewed at his lip, one thing instantly popping to mind but Cas was already buying him so much, he didn’t want to seem greedy. He replied, “No, that’s it.”

The raven leveled a stare at him, “Dean.”

The blonde sighed, “I’d really like a new leather jacket. The one I have is getting really worn.”

“We will also need a leather jacket and a casual jacket for him to wear as well. Can you guys do that for us,” the man asked casually.

Everyone jumped into action. This time, there were a lot less items being shoved in Dean’s face and he was able to give his opinion on things he liked and disliked. He felt much better and didn’t seem like he was about to run away. Three hours later, Dean and Cas walked out the store laden with shopping bags. Some things were going to be delivered to the hotel such as the suits, but Dean wore his new jacket out the store.

As they walked down the street, the assassin saw a store he recognized. He smirked as he walked towards it. Cas looked at him as the man entered, his head held high like he owned the place.

Dean was overjoyed when he saw that the two shop employees were the same from yesterday. “Hello sir, how can we be of assistance,” the female asked.

“You work on commission right,” the assassin asked.

The male spoke up, “Yes that’s right.”

Dean slid the glasses he was wearing onto his head. He held the bags on his hands out for emphasis and said, “Remember me from yesterday? You wouldn’t help me because you said I couldn’t afford anything?”

Both employees’ eyes went wide at the sudden realization. The woman gasped before saying, “Well, yes we remember you.”

Dean snorted and smiled brightly before replying, “Yeah, well big mistake. Huge actually. Told you I had the money.”

Dean slid the glasses back down and walked out, leaving the two with their mouths hanging open. He sidled up to Cas and they continued their walk down the street. Later they stopped in a park and Cas was leaning against a tree with Dean lying comfortably in his lap. They were munching on hotdogs that the assassin had bought from a nearby vendor.

“I can’t remember the last time I had such carnival food. It really is quite good,” the raven commented.

“Heck, that dinner we had last night was like nothing I’ve had before. Some of it was really good, some of it not so much. Like those oysters, way too slimy,” Dean made a disgusted face.

The other man chuckled, “They are certainly an acquired taste. I’m glad that overall, you enjoyed the food.”

“Way better than most of the company. Your brothers are conceited assholes, not to be rude,” the blonde said frankly.

Cas nodded in agreement, “I can’t argue. Michael and Lucifer have been like that their whole lives. Gabe does anything and everything to piss them off and solidify just how far from our family’s grace he has fallen. The only reason Michael and Lucifer put up with him is because I’ve given them all a decent sized share of my company and they are on the executive board, so they have to be included in all the meetings.”

Dean looked at him surprised, “Why would you give any of them a part of your company except for maybe Gabe?”

“They are family Dean. It was only right,” chided the older man.

“Fuck that Cas. A wise man once told me family don’t end in blood, but it doesn’t start their either. Family cares about you, not what you can do for them. Family’s there, for the good, bad, all of it. They got your back, even when it hurts. That’s family,” Dean said with a firm finality.

Cas sat there, impressed by the blonde’s speech. “I never really thought of it like that. Maybe, maybe you’re right Dean. Lucifer and Michael have never really acted like family, especially after I moved to America. Gabe is Gabe but he has always had my back if I truly need him.”

“I’m not saying none of them are family, I’m just saying you don’t owe your business to them just because they are biologically related to you. Some of the people I would die for don’t share a drop of blood with me,” the blonde replied.

“You’re right Dean. Sadly, I don’t think I could just cut my brothers out of the business now though. Whatever brother killed Anna will certainly lose their share.”

“I would hope so.”

Cas smiled, “Yes, so would I. It’s getting late, are you ready to head back to the hotel?”

“Yeah, let’s get going. It’s been a long day.”

They headed back to the hotel. They settled on the couch and watched TV until they ordered dinner. After dinner, Dean turned to the other man on the couch. He reached out and stroked his finger down the side of Cas’ face until he could cup the man’s jaw.

The Russian turned his head slightly so their eyes locked. He gave a small smile before asking, “Yes Dean?”

The blonde smiled back and suggested, “It’s been a long day. How about we go relax in the bathtub or something?”

“That sounds wonderful. Go start the water. I’ll be in there in a few minutes.”

Dean nodded before standing up and walking away. Cas’ eyes followed him, taking in the wonderful view of the man’s body. Cas had to drop his eyes as he sighed. He didn’t want to admit it, but he felt something for the younger man. Something he had never felt before and shouldn’t be feeling for a random prostitute off the street. There was something about Dean that drew Cas in like a moth to a flame. The blonde was charismatic, endearing, funny, gorgeous, and so carefree. All things Cas had never been and would never be able to be.

Cas sighed heavily once more before getting up and following the other man. When he walked into the bathroom, Dean was already relaxing in the tub. The tub was only a quarter of the way filled and there were already hundreds of little bubbles in it.

The Russian leaned against the doorframe, “You know, you really just don’t strike me as a bubble bath person.”

“Is it because of my rugged good looks and devilish charm,” Dean said with mock laughter.

Cas rolled his eyes as he started to strip, “That’s it exactly.”

As soon as he was naked, he stepped into the tub and slowly lowered himself until he was sitting between Dean’s legs. He leaned back and rested his head against the hard chest of the man behind him. Dean brought his hands up to Cas’ shoulders and started massaging them and his back.

The raven moaned in pleasure, “My God, that feels delectable. Keep doing that and I might have to keep you.”

He felt the hands falter for a second but then they resumed their normal pace. “Haha, Cas. I told you I was gonna treat you good. Now, just relax, you’ve got some serious tension in these muscles.”

“I can’t imagine why. My father wants me to take over a family business I have no interest in taking over, my sister was murdered barely more than two weeks ago, one of my brothers is the reason for her murder, and I still haven’t figured out exactly what brother betrayed his own family,” Cas listed off, anger filtering into his voice.

Dean started peppering kisses to the man’s stiff shoulders as he continued to massage, “Hey, I wasn’t saying you didn’t have reasons to be stressed. We are going to figure out who killed Anna, I promise. The other part I can’t help you with. If your dad let you leave Russia in the first place, I can’t imagine he would force you to take over the business. Just tell him the truth.”

“If only it was that easy. Thank you, Dean, but nothing in my world is that simple,” the raven lamented.

The blonde didn’t know what else to say so he just continued his massage while the Russian slowly relaxed against him more and more. The two men enjoyed the closeness of each other most of the bubbles had popped and the water had run cold. After quickly bathing, Cas stood up and stepped out the tub. Dean was mesmerized as he watched water run down the man’s toned body. He licked his suddenly dry lips.

Cas noticed the motion and held his hand out for the blonde to take. Dean took it and was pulled to his feet and out the tub. The Russian grabbed a towel and dried them off. Once they were both dry, he dropped the towel and latched his lips to the juncture between Dean’s neck and shoulder. The assassin let his head drop backwards as the man nibbled on his flesh.

Cas pulled away after he had left a rather impressive hickey. His eyes had darkened with lust and in a husky voice he said, “I want to fuck you Dean.”

“That’s what I’m here for Cas,” the blonde whispered back.

The Russian growled before shoving the other man until his knees hit the bed and he fell backwards. Dean’s eyes were blown wide with lust and Cas licked his lips in appreciation. He watched as the blonde started stroking his cock slowly, the flesh hardening beneath his fingers. Cas watched as precum formed at the tip and then was rubbed into Dean’s flesh as he used it for lube.

Cas went to his bag and grabbed a bottle of lube and a condom before returning to his spot at the end of the bed. He reached out and wrapped his large hands around Dean’s slim waist and pulled the man down the bed until his ass rested at the edge and his legs were thrown over the Russian’s shoulders. Cas popped the top on the lube bottle and squirted a decent amount in his palm. He closed the bottle and dropped it to the floor.

He dipped his fingers in the lube before rubbing it between them, helping to warm it up. He then brought one lubed finger to Dean’s puckered entrance. He pushed against the muscle and watched as Dean’s body sucked the digit in.

The blonde threw his head back as he continued to pump his cock, “More, Cas, I can take more.”

The Russian obliged and added a second finger. He pumped the fingers in and out, marveling at how warm and tight Dean felt around them. After a few thrusts, he moved his fingers apart, slowly stretching the blonde’s hole.

Dean grunted and tried to rock down onto the fingers inside of him. Cas let Dean fuck himself a few times before adding a third finger. The blonde arched as he was filled more completely. He started pumping his cock faster as he continued to rock his hips against Cas’ fingers.

“Cas, I need you in me; I’m stretched enough man,” Dean begged.

The raven thrust hard against the other man’s prostate and the blonde keened low in his throat at the pleasure. “You want my fat cock inside of you? You want me to split you open and fuck you until you can’t even walk malen'kiy,” the Russian asked in a raspy voice.

Dean thrashed his head, “Yeah, Cas, I want you to fuck me with that big cock of yours so that I feel it for days. Give it to me, please!”

Cas pulled his fingers out and wiped them against the comforter. He grabbed the condom package and ripped it open. He slid the condom onto his erection and used some of the extra lube to slick himself with. He stroked his own cock a few times before lining it up with Dean’s entrance.

He pushed in with one firm thrust. He didn’t stop until his balls slapped against Dean’s ass. The blonde arched his whole body as he was filled. Cas had stretched him well, but the man’s dick was bigger than his fingers. As Cas filled him, his body was swamped with pleasure and just a bite of pain.

Both men were panting as Cas set up a brutal pace. He gripped Dean hips hard and started fucking into him. The blonde met him thrust for thrust. The only sounds in the room were their grunts and the sound of skin slapping skin.

Cas pulled Dean closer to him and the new angle allowed him to fill the blonde deeper and ram his prostate with every thrust. Dean’s mouth formed a perfect “O” as waves of ecstasy crashed through him. He pumped his cock harder as he felt his balls tightening. With a few more thrusts, Dean felt his orgasm crash into him. Ropes of cum landed on his stomach and chest. He came so violently, that some drops even landed on Cas. The raven thrust even harder until with a shout, he curled over Dean and came hard.

Only their rapidly rising and falling chests moved as the two men came down from their highs. After a few minutes, Cas’ cock softened, and he pulled out of Dean. The blonde moaned at the loss of being full. His legs dropped from the raven’s shoulders and hung over the edge of the bed. Cas went and grabbed a rag to wipe Dean down. Once done, he collapsed into the bed next to the blonde.

Dean rolled onto his side so they were facing each other, “I have to say man, you are by far one of the best lays I’ve ever had.”

Something flashed in the other man’s eyes, but Dean couldn’t decipher it. “How many people have you been with Dean?”

Dean huffed, “Hell if I know. I’ve been doing this for years.” But Dean did know. He kept a tally. The number was lower than what most of the people in H.C. would guess, especially since that’s how he got his name. He didn’t sleep with every target just the ones he couldn’t close enough to on his own. The assassin had fucked twenty-nine people over the years.

“How did you even get into this life,” the man asked curiously.

Dean sat up and brought his knees to his chest so he could rest his chin on them. He was quiet for a long time and Cas wondered if he was going to answer the question. The Russian sat up when he saw a tear falling down the man’s cheek.

“Dean, I never meant to upset you so much. You don’t have to tell me.”

“What do you mean? I’m not upset.”

Cas collected the tear on his fingertip, “You’re crying.”

Dean looked at him in horror as if that single tear was going to kill him. The man jumped from the bed and rushed into the bathroom. He stared into the mirror and rubbed at his face. He walked out, wrapped a robe around him, and headed out the bedroom.

The Russian shouted after him but if Dean heard him, he ignored the calls. Cas grabbed a robe and clothed himself before following the distraught man. He found him on the balcony overlooking the town.

Dean paid him no mind as he joined the man outside. Cas placed a hand over the other man’s, but Dean didn’t even stir.

“I’m sorry. I didn’t know it was such a sensitive topic. I never would have brought it up had I known,” Cas said, a hint of pleading in his voice.

Dean gulped, “It never has been before. I haven’t cr… cried over my family since the day they were buried.”

“You’ve held that grief in for how long?”

“My parents were murdered seventeen years ago tomorrow. It will be that long for my brother a week from today. My brother was kidnapped and when, uh, the cops found him, he was gone,” Dean stared stoically straight out in front of him, refusing to look at the other man.

He hid the sadness well, but Cas could see the telltale signs of Dean’s grief. The fingers that rested against the balcony wall trembled, his voice shook, he kept gulping air, trying to prevent the unshed tears from falling. When he took a deep breath, it rattled through his whole body.

“I’m so sorry Dean. You couldn’t have been more than a child.”

“I was ten. I, uh, got put into the foster care system. I was too old by then, nobody wanted me. When I was eighteen, I struck out on my own. Hit some hard times and I didn’t have anybody to turn to. I’ve always had a pretty face and a nice body. I got my first John and I just kept doing it. The money was good,” the lie flowed off his tongue.

Cas moved closer until their hips were touching, his arm moving to wrap around the man’s waist, “Why did you agree to this deal when the anniversary of their deaths was so close. Surely, you must have wanted to spend the time with someone else besides me.”

Dean shook his head, “No, I need to be working. If I don’t, then the grief consumes me, and I can’t think or breathe. If I’m working, then I don’t think about it.”

“Dean, you need to let yourself grieve so you can move on. It’s obvious their deaths still haunt you and they never won’t until you let yourself feel whatever it is you need to feel,” Cas spoke softly.

The blonde turned to him, fire in his eyes, “You have no clue what you’re talking about! If I let those memories in, they’ll drown me!”

Cas nodded before looking out over the city, “You will feel like you’re drowning. You’ll feel as if you’re treading water and at any minute, you’re gonna sink below and never get another breath of air. Let me tell you, you will eventually get air, you’ll come to land, and you’ll be able to walk forward.”

Dean lashed out, “Yeah, how would you know.”

Cas looked at him, fury radiating from his body, “Because I know what it feels like to lose a mother and a sister. I know what drowning feels like. Obviously, you forgot that. Maybe you should just leave Dean. You haven’t seemed to pay attention to anything I’ve said so far.”

The Russian turned to walk away but Dean grabbed his arm, “I’m sorry Cas. I’ve never felt like this, so uncontrollable and I wanted to lash out. I didn’t mean it. Of course, I remember what you’ve told me about your family.”

Cas sighed heavily before turning back to the upset man, “Let me help you Dean.”

A single tear slid down the assassin’s face, “I don’t know how. I’ve never really taken help from people.”

Cas pulled the shaking man into his arms, “Just let go Dean, just let go.”

They stood there in silence for moments before a sob was ripped from the blonde’s throat. He melted against the older man as sob after sob was let loose. He cried for the death of his parents and his brother. He cried at the brutality of their murders and the unfairness that he had to live in a world without them. He cried for the childhood he had lost and for the future his family never had.

Through it all, Cas held him, through the sobs, snot, hyperventilating, and the complete and utter breakdown that Dean had, Cas was there for him. After minutes, the tears started to slow and finally they stopped. The assassin was completely pliant in the other man’s arms as he walked through the suite and back to the bedroom. He sat Dean gently on the bed and disrobed the man. Cas helped him to lie down and then tucked the blanket around him. Through it all, Dean didn’t make a sound or even move. Once he was tucked in, he fell asleep almost instantly. Cas knew just how exhausted one could feel after working through their grief.

He was startled when he heard a phone ringing. It wasn’t his and he looked throughout the room, trying to locate Dean’s phone. He found it still in the pocket of the pants he had worn that day. He thought about waking the blonde up but knew he was in no shape to try and answer a phone call.

“Hello, this is Castiel. Dean can’t come to the phone right now, could I take a message?”

“What do you mean Dean can’t come to the phone? Where the hell is he, what did you do to him,” an irate female voice shouted at him.

“Please quit shouting. First of all, who are you?”

“I’m Charlie Bradbury, his best friend. He was supposed to check in with me today, but he hasn’t and I’m just trying to make sure you didn’t go psycho and kill him.”

Cas chuckled, “If I did kill him, which I didn’t, do you think I would admit to it?”

There was some stuttering on the other line before, “Well, no but still. Why didn’t he check in with me?”

“Dean has been very busy today. We spent the day out and we spent the evening enjoying one another’s company. Recently, as in about ten minutes ago, he had a very strong sobbing session,” Cas explained.

“Now I know you’re lying. Dean never cries let alone sobs.”

“A person tends to have a pretty strong reaction when they finally face seventeen years’ worth of guilt and sadness that they’ve kept locked away since their family died,” the Russian replied.

“Wait, what? You got Dean to talk about his feelings,” the woman asked surprised.

“I wouldn’t say he talked about them so much as cried about them. And now he is asleep, recovering from such an emotionally taxing event.”

“How in the world did you get him to address it? No one had been able to do what you accomplished?”

“I told him I knew what it felt like and had already experienced it. He understood that I wouldn’t think any less of him nor that I would leave him alone,” the Russian replied.

“Well neither would I or any of his other friends and family,” she said sounding insulted.

“Have any of you went through what Dean or I did? Do any of you know what it feels like to have your family violently ripped from you without any chance to say goodbye,” the raven asked stoically.

There was a pause, “No, I guess we don’t. I lost my mom, but she was in a coma and I got to spend an afternoon with her saying goodbye on my terms.”

“Exactly, it was on your terms. Dean didn’t have that. I’ll make sure to have him call you tomorrow and check in Ms. Bradbury.”

“Uh, thanks. You know, you’re not that bad. The nicest person Dean has ever been with.”

“Thank you for the compliment. Good night.”

“Night.”

Cas hung up the phone before crawling into bed. He had just gotten comfortable when an arm was thrown around his waist and a cheek rested on his chest. He smiled and wrapped an arm around the sleeping man. It was the best sleep he had in a long time.

The next couple of days sped on by. The business dinner party went smoothly, everybody eyeing Castiel’s newest arm candy. Dean spied on Michael and Lucifer, but they still didn’t give up any valuable information. Cas was frustrated but Dean said they would come up with a plan. The day after the party, Cas went to work, and Dean lazed around the suite. He called Charlie to check in and he even called Ellen.

He thought she would be furious, but she was just glad to know he was ok. She wanted him to come home and he promised he would once he finished his deal with Cas. Ellen actually gave him an ideal of how to weasel the guilty brother out. When the Russian arrived back to the suite, Dean shared the plan.

“Hey, so I have an idea of how we could get your brother to confess.”

Cas sat heavily on the couch next to the blonde, “How is that?”

“Well, you think they killed Anna to lure you home and to get you to sign over your father’s business, right?”

“Yes,” the man replied slowly, unsure of where Dean was heading.

“What if you announced that you are going to take over your father’s company,” Dean said with a smirk.

“I already told you I have no desire to do so.”

“I know that. You aren’t really going to; you’re just going to say it. It might lure your brother out. He might come face to face with you and demand you sign the company over. It might be the only way to make him desperate enough,” the blonde explained smugly.

“What if he just harms or kills someone else to try and get me to sign the company over,” Cas asked skeptically.

“Besides Gabe, is there anyone else you’re close to? Make sure Gabe is protected and then he will have to come to you. I think it’s the best shot we got,” Dean said trying to convince the Russian.

Cas thought about the proposal. “I fear you might be right. It is a good plan. I will call Gabriel and see what he thinks. We could arrange something and have me announce it to my brothers.”

“Exactly. It’s a good plan Cas. The least we can do is try, right?”

“Yes, it’s the least we can do.”

“Alright, so call Gabriel and see if you guys can’t set something up.”

Cas pulled his phone out and called his brother. He explained Dean’s plan and his brother agreed with the blonde that it was their best shot at outing their brother. Gabe said he would call a family dinner at his place on Friday which was the day after tomorrow. Cas would make his big announcement and they would wait and see what happened.

Once Cas hung up, Dean asked, “So what’s on the agenda for tomorrow?”

The Russian smiled, “I am taking you somewhere special. I figured we could spend the day together since I don’t have any meetings.”

Dean blushed, “You don’t have to take me anywhere.”

“I want to. Now, let’s head to bed. I’m exhausted.”

Dean wriggled an eyebrow, “No fun times tonight.”

The man chuckled, “No, no fun times.”

Dean pretended to pout but followed Cas to the bedroom. The blonde woke a few hours later to an empty bed but could hear noise from the living room. He grabbed a robe before heading out the bedroom. He stopped when he realized the noise was the piano that Cas was currently sitting at. He didn’t even know the man could play let alone sound so good.

Dean walked over and sat on the edge of the bench Cas was on. He watched the man play for minutes until a final note rang through the air. Cas looked towards him and their eyes locked.

“That was beautiful; you’re amazing,” Dean complimented.

“Thank you. My mother taught me how to play. It’s something I have to remember her by and a way to keep her close.” Cas’s lips moved into a one sides smile, “Anna used to love to sit and listen to me play. I guess after making you face your past, my own past crept up a little.”

“If you need to let out, I’m here,” the assassin offered.

Cas held a hand out and Dean took it. Het let the older man position him however he wanted him. Cas scooted the bench back so that the blond was standing directly in front of him. Dean leaned against the keys but made sure not to sit on them. The Russian untied the belt of the robe and let it hang open. The blonde was clad in nothing but his boxers beneath.

Dean hitched a breath as Cas ran gentle fingertips down his body. The raven started at his shoulder, went over his nipples, down his belly and stopped right at the waistband of his boxers. The older man leaned forward and took one of the blonde’s nipples in his mouth and sucked. Dean dropped his head back as the bite of pleasure. Cas repeated the motion with the other before kissing his way down the assassin’s stomach. He swirled his tongue around the man’s belly button before continuing lower. He reached his fingers up and pulled the underwear down until his cock sprang free and slapped against his belly, a drop of precum already forming at the tip.

Cas leaned forward and kitten licked at the younger man’s erection. Dean gasped as his lips finally closer over the head of his dick. He reached out and grasped at the raven locks, forcing Cas’ mouth further onto his erection. Cas hollowed his cheeked and increased the pressure on Dean’s dick causing the man’s hips to buck forward.

Cas held a hand up and placed his fingers at Dean’s lips. The man greedily sucked them in and coated them in his saliva. Cas pulled away and snuck his into the back of the blonde’s underwear until he could circle his spit-soaked fingers around the other man’s entrance. He slowly pushed one finger inside the tight muscle. He pushed until his finger was buried to the knuckle before slowly sliding back out and pushing back in. Once he felt Dean was loose enough, he pushed another finger in and started scissoring them, stretching the tight muscle further.

Dean moaned in pleasure as his senses were assaulted from both ends between the mouth on his cock and the fingers in his ass. He tightened his fingers in Cas’ hair as he panted, “Gonna cum Cas, so close, just a little more.”

Cas smiled around his mouthful and added a third finger. Once he could move his fingers in and out smoothly, he picked up the pace slamming them inside the blonde’s willing body. Dean shouted out and he aimed for the same spot, thrusting his fingers against the man’s sensitive prostate. He increased the pressure even more around Dean’s cock and with a few more thrusts of his fingers, the man shot his load into Cas’ mouth. He drank it all down, not even letting a drop escape. He continued to suck the man’s cock and lazily pumped his fingers inside of Dean until the man’s flesh softened and Dean’s moans of pleasure turned into groans of oversensitivity.

He left the softened flesh slip from his mouth and he pulled his fingers out, wiping them on the robe to clean them off. He stood up and pulled Dean close to him pushing the robe off his shoulders and having the man’s underwear pool at his feet. He guided the blond until he could life Dean up and sit him on top the piano.

“Cas, what are you doing? I don’t wanna break this thing; I can’t imagine how much it costs.”

The Russian smiled as he positioned Dean where he wanted and forced him to lie back until his back was flush with the wood. The blonde flinched at the coldness. “Don’t worry malen'kiy, you aren’t going to break the piano. They are sturdier than what you think. Now, stay, I will be right back.”

He returned a moment later, completely naked, a condom rolled on and his erection shiny with lube. He pulled Dean’s legs onto his shoulder before lining up with the man’s slick entrance. He pushed in slowly, not wanting to hurt the other man. The blonde groaned at the feeling of being full and arched slightly forcing the other man’s cock into him even more.

Cas stilled only when he was fully seated inside of Dean and waited for the man to adjust.

The blonde looked at him, “Cas, fuck me, please! I want it!”

Cas did as told. He pulled out and slammed back in, pushing the blonde further up the piano. Cas grabbed at Dean’s hips forcing the man back down onto his cock. He continued to thrust into Dean, finally finding his prostate and causing the man to cry out.

“God Cas, feels so good! I’m already getting hard again,” the blonde grunted in between thrusts.

Cas grunted, “Touch yourself, I want to see you cum again.”

Dean quickly wrapped a hand around his hardening flesh and timed his strokes perfectly with Cas’ thrusts. He felt his balls tightening and knew he was close. With one more well aimed thrust from Cas and his fist increasing the pressure on his cock, Dean came for a second time that night. Cas thrust a couple more times before bending over Dean and filling the condom with his seed.

They stay that way for a few minutes, letting their heartbeat slow down. The sweat cooled on their skin and Dean could feel the cum cooling on his stomach. Neither of them cared enough to move until Cas’ cock slipped out of him and he immediately missed the feeling of being full.

The Russian stood up and rolled the condom off his cock before tying it up and dropping it into a garbage can. He grabbed some napkins and hastily wiped Dean off before tossing them in the trash as well.

The blonde sat up, “Thanks for always cleaning up. I’ve been with some people that as soon as they are done, they stand up, get dressed, drop the money down, and walk out before I’ve even caught my breath.”

Cas sat on the couch and motioned for Dean to join him. The blonde hopped off the piano and curled up next to the other man. Cas wrapped an arm around him, and the blonde rested his cheek on the man’s shoulders.

They ended up falling asleep just like that. They didn’t wake until late next morning when the sun was already up and shining. Dean blinked his eyes open, slowly waking up. He tried to get his bearings. Somehow through the course of the night, Cas had ended up laying down and Dean was almost completely laying on top of him.

**Notes for the Chapter:**

> 1 more chapter to go and this story will be wrapped up!


	3. The End

**Summary for the Chapter:**

> Cas takes Dean out on a special date. With some help, Dean figures out a way to determine which brother had Anna murdered. Cas and Dean figure out the truth but Cas also learns the truth about Dean; can their blossoming relationship handle the truth?

**Notes for the Chapter:**

> Here is the final chapter!

The other man groaned before muttering, “Good morning Dean.”

“Morning Cas, you know you make a comfy pillow,” the blonde joked.

“Don’t patronize me or you might find yourself on the floor,” the man grumbled as he partially stretched, and the sounds of popping bones could be heard.

Dean chuckled as he stood up and did his own stretching. He realized he was still naked and walked over to where his underwear lay and slipped them on. He tossed the robe to Cas since the man was also still naked from their intimacy the night before.

The blonde headed to the en suite kitchen and started the coffee maker. A few minutes later he poured a cup and asked Cas if he wanted any.

“Yes, fill the cup up halfway with coffee and the rest with milk. Add three spoons of sugar to it please,” the man responded still lying on the couch.

Dean frowned at the drink, “Cas, why not just drink milk and sugar instead of coffee?”

“Just bring me my damn coffee Dean,” the man grumbled.

The blonde rolled his eyes as he walked back over and waited for the man to sit up before handing him his drink. He took a seat back on the couch and took a sip of his coffee. He smiled as the hot liquid slid down his throat and slowly warmed up his body.

“So, you never did tell me what we were doing today,” Dean commented nonchalantly.

“No, I didn’t and I don’t intend to still. I like the element of surprise. Would you like me to call room service and have them deliver us breakfast?”

“Meh, I don’t normally eat breakfast all that much so I’m good but if you want something, go right ahead.”

Cas took another sip of his coffee, “I’m not usually much for breakfast either. After we finish our coffee, we will head out.”

The limo pulled up outside a large racetrack. Dean’s eyes widened in delight. He had had a love for cars all of his life and had always wanted to attend a Nascar race. He turned to the raven, excitement written all over his features.

“You brought us to a racecar event? Dude, I’ve wanted to come to one of these for my whole life! This is awesome,” the blonde rambled as he exited the car and waited for the Russian to join him.

“I’m glad you approve. I figured you must love them since you knew about my car and especially after retrieving your Baby, as you called her. She is very impressive,” the other man commented as they headed towards the entrance.

“Thanks Cas, she’s my pride and joy. I rebuilt her when I was fourteen. I couldn’t imagine if anything happened to her,” Dean admitted as they headed inside.

Cas grabbed his elbow and lead him towards a private entrance. Dean wasn’t even surprised that they had their own special reserved seats. They walked down a dim hallway before going through another door and the blonde blinked at the sudden rush of sunlight. They were sitting in an enclosed booth that overlooked the whole racetrack.

Dean immediately went to stand in front of the glass and gaze at everything before him. He could see the cars already lining up on the track, the pit crews all waiting anxiously in the background, the stands were loaded with cheering fans, and if he looked closely, vendors walking up and down the aisles selling different things.

Cas walked up behind him, dragging two chairs. He sat in one and motioned for Dean to do the same. As they both sat, the Russian handed him a beer and the blonde then noticed the table of food and bucket of beer nestled in the corner.

“Thanks, Cas. Man, this is awesome, best day of my life and it’s just started. Have you ever even been to one of these before,” Dean asked as he took a drink of his beer.

The raven shook his head, “No, never. I can appreciate a car, but they have never been of huge interest for me. I’ll be honest, watching cars drive in circles never held any appeal.”

Dean looked at the man, “If you have no interest on this, then why did you bring me here?”

Cas gave a small smile, “Because I knew you would enjoy it. I wanted to give you a small treat for everything you’ve helped me with so far.”

The blonde didn’t say anything but felt something stir inside of his chest. He chose not to think about it and locked it away. Dean drunk his beer and people watched until the announcer came over the speaker system and said the race would start in five minutes.

Throughout the race, Dean was enraptured. His eyes hardly ever left the track below as the cars raced around the oval over and over again. Cas had attempted to watch the race but after watching the cars complete the tenth lap, he was already bored. So, he chose to watch something else instead.

The man in front of him was the most beautiful creature he had ever seen. With his dirty blonde hair, muscular body, hundreds of freckles, and eyes greener than an emerald, Dean was absolutely stunning. It wasn’t just his looks that captivated the Russian. The other man was funny, charismatic, charming, wicked smart, and caring. Cas had never met another man who would have been so willing to risk his life just to help a stranger out. It was no wonder he was slowly falling in love.

That had to be the most absurd thing in the world. Cas, the son of famous Russian Mafia don, Chuck Krushnik and the CEO of Humble Bee, a multi-million dollar corporation and he was falling in love with a prostitute that he had picked up off the street. He knew Dean hadn’t explicitly chosen the life he led, having fallen into the lifestyle because of such an awful childhood. He didn’t blame the man for what he did, how could he when it was the sole reason they met.

“Hey, Cas, this is it, it’s the last lap! Fifty-four has it in the bag,” Dean cheered as the cars crossed over the finish line. The blonde stood and cheered with excitement as the race finally came to a finish. He turned to look at Cas, his eyes shining, and his cheeks flushed with excitement.

Cas smiled and Dean moved closer to him and the Russian couldn’t help but reach out and cup his jaw. The blonde licked his lips and Cas watched the motion like a hawk. Dean glanced up, his eyes locking with the other man’s. Cas felt his heartrate kick up and he leaned forward, not even thinking about what he was about to do.

The two men were mere centimeters apart when the door was opened. The two men were startled and jumped apart.

“Oh, sorry, I’m looking for the bathroom and all the doors in this hallway look the same,” said an impeccably dressed woman.

She quickly shut the door, but the moment had been lost. The two men smiled awkwardly at one another before throwing their empty beer bottles in the trash and walking back to the limo. They headed back to the hotel. Cas told Dean they had enough time to shower and get dressed before they were heading out again.

“How am I dressing up Cas,” the blonde asked as walked into the bedroom, a towel wrapped around his waist.

“A suit and tie if you don’t mind.”

“You’re the boss. Which one would you like me to wear? The gray or the black one,” he asked as he stood in front of the closet.

Cas thought for a moment, “The black one.”

“Aye aye captain,” the blonde joked as he pulled the suit out.

Ten minutes later and the blonde was standing in the mirror looking at his reflection. He had to admit, he looked pretty damn good. The pants were hemmed to fit him perfectly. He had a white dress shirt underneath a black vest and a red and gold tie around his neck that Cas had picked out. To top it all off, he had a black jacket over it all that he let hang open.

He turned around to face the Russian and was glad when he saw the man nod in approval. Cas picked up a rectangular box before walking over. He opened the box for Dean to look inside. The man gasped at what he saw. Nestled inside were a pair of golden cufflinks inlaid with a circle of diamonds and a ruby in the center. Dean reached out to touch when the lid was closed on top his fingers. He pulled back before looking at Cas and chuckling at the man.

He opened the box back up, “I think these will match your tie wonderfully. They are on loan so please be careful not to lose them.”

Dean swallowed thickly before looking up, “How much would they cost if you were to purchase them?”

Cas smirked, “One-hundred thousand dollars.”

The blonde balked, “Holy shit. I’m not sure if I want to wear them, I’m afraid of losing them!”

Cas took them out and gently attached them to Dean’s suit. “You’ll be fine. There, you look spectacular.”

The assassin rubbed at the back of his neck nervously, “Thanks Cas but you look pretty damn good yourself.”

The other man said not another word as he offered his arm. Dean took it and they headed downstairs. As they walked through the lobby, heads turned in their direction, but they weren’t the hateful stares or the judgmental glares Dean had become accustomed to. This time, as the other hotel patrons looked at him, it was with envy. Every hotel employee had a smile on their face as they watched the couple. Dean caught sight of Rowena and even she seemed to approve of his new look.

They headed to the limo and rode in silence until they pulled outside of a single plane. Dean stiffened as the car stopped. Cas slid out the seat and stood waiting for his companion. The limo driver held the door open, but Dean sat frozen. His heartrate had picked up and he felt beads of sweat rolling down the back of his neck.

He was broken from his trance when Cas leaned inside the open door and asked, “Dean, is everything alright?”

He licked at his suddenly dry lips and shook his head, “No, I’m…I’m…I’m petrified of flying.”

A frown crossed the other man’s face, “I had no idea. Our plans for this evening require us to fly as we won’t make our reservations in time by driving. The flight will only be an hour.”

Dean locked his wide-eyed gaze with the other man, “You promise it will only be an hour.”

“I promise, trust me Dean.”

The blonde slowly slid out of the car. He stood there unmoving, looking at the plane with trepidation. He flinched when Cas took his hand and slowly started to lead him forward. The closer they got, the more frightened Dean got.

He stopped right at the stairs leading into the cabin, “Cas, I can’t do this!”

The other man turned to face him. He cupped the blonde’s jaw, “Yes you can. I’ll be right here with you, nothing will happen.”

Dean took a few panicked breaths before gripping Cas’ hand tighter and letting himself be led onto the aircraft. They settled in their seats and Dean gripped one armrest, his fingers digging into the fabric and turning bright red. The other hand was tightly squeezing Cas’ He started humming low, trying to calm his racing heartbeat.

Cas tilted his head as he stared at the man next to him, “Are you humming Metallica?”

Dean gave a slight nod, “It calms me down.”

The Russian pulled their joined hands towards himself before placing a few kisses to the blonde’s knuckles, “It’s alright malen'kiy, I’m not going to let anything happen to you.”

Cas kept talking to Dean as the plane rolled down the runway before taking off. The next hour was tense, the blonde never truly relaxing until the aircraft had landed and they were driving in a limo towards the restaurant.

After dinner, they got back in the limo and Dean hoped they hadn’t flown just to get food. He found out soon enough just where they were headed. The limo stopped outside a huge theater, throngs of people gathered outside.

The blonde turned to look at his companion, “What is this?”

“It’s the movie premiere for the new Marvel movie. I know a few people,” the man smiled.

“Dude, you’re taking me to the opening night of Avengers Endgame! What kind of people do you know,” the assassin asked astonished.

“Robert Downey Jr. has a monthly subscription of honey delivered straight to his place from the factory,” the other man said as if was nothing.

“You know RDJ? Holy crap Cas!”

Before anymore could be said, the door was being opened and Dean and Cas shuffled out the limo. They walked through the crowd weaving in and out of fans and reporters before stopping near the entrance.n

Cas heard his name shouted and both me turned. Dean felt his knees going weak as he recognized the man walking towards them. Iron Man himself was striding towards them, a pair of red sunglasses over his eyes.

“Castiel, good to see you. Your honey is as phenomenal as ever. And who is this handsome man?”

The Russian smiled as he introduced Dean, “This is my date for the night, Dean Winchester.”

RDJ held his hand out and the blonde felt as if he was on cloud nine as he shook the actor’s hand, “Oh my gosh, I can’t believe I’m getting to meet Iron Man. Huge fan, love all of your work.”

Dean blushed at his rambling but the actor only chuckled. “Nice to meet you. Here, why don’t you keep track of these for me?”

Downey took the sunglasses off his head and pulled a sharpie out of his pocket. He wrote something on the lens before handing them to Dean. The blonde could only stare in wonder as the actor said his goodbyes and made his way back to the red carpet.

The younger man looked at the raven, “I just met Robert Downey Jr. and he not only gave me his sunglasses but also signed them. Could this night get any better?”

Cas chuckled, “Do we even need to watch the movie?”

Dean looked up sharply, “You bet your sweet ass we do!”

The Russian rolled his eyes as they headed inside. The movie was phenomenal, the best Avengers movie to date even if it left most of the audience crying at the death of such a beloved character. Dean wasn’t even ashamed of the tears that fell down his cheeks. As usual, Cas watched the man next to him more than the actual movie.

After the movie, they headed to an after party and Dean was in heaven as he got to meet many of the actors from the movie. He was on cloud nine and not even the plane trip home could deter from his mood. As they walked into the suite, Dean was still floating.

He turned to Cas, “This had been the absolute best fucking day of my life! How can I ever thank you enough?”

“I’m glad you enjoyed it so much. It’s payment enough having watched you enjoy yourself.”

Dean slipped his jacket off and sat it back on the chair before loosening the tie and draping it over the chair as well. He then fell onto the couch, a smile permanently etched on his face. Cas dropped his jacket and tie off before joining the younger man.

They sat there staring at one another. Dean’s eyes were shining, and he may have been a little tipsy from the alcohol he had consumed. Cas’ eyes were no less bright, but he hadn’t drunk too much throughout the night.

Neither one could say who moved first but one moment their eyes were locked and the next their lips were moving against one another. Dean tilted his head and slightly parted his lips. Cas took the opening and thrust his tongue inside the other man’s mouth. The blonde groaned as the older man invaded him mouth, practically claiming him in the process.

Cas broke the kiss so he could stand up. He reached a hand out and pulled the blonde to his feet. They were then kissing again. Cas ran his hands down Dean’s body until they could cup the man’s ass. Then, in an impressive show of strength, he lifted the blonde clean off the floor. Dean instantly wrapped his legs around the other man’s waist as he walked to the bedroom.

He deposited the younger man on the bed gently before leaning over and kissing him once more. His hands made quick work of Dean’s vest and shirt, untucking them and then pulling them over the man’s head and dropping them to the floor. Dean returned the favor, so they were now both bare from the waist up.

Dean reached out and pulled the other man on top of him so bare skin slid against bare skin. They kissed again, battling for dominance. The blonde finally gave in and relaxed back, letting the older man take control. Cas sat back and reached for the blonde’s trousers. He quickly divested him of the rest of his clothes as well as his own.

They both gasped as their cocks slid against one another. Cas reached down and grasped both in his large hands before starting to pump them slowly. Dean dropped his head to the pillow in bliss.

“Cas, more, please, I need more,” the blonde begged.

“I need to get condoms and the lube, but I have no desire to leave from this bed,” the man said huskily.

Dean wrapped an arm around the man’s neck and pulled him in for another kiss before whispering, “Then don’t.”

“We can get away with spit as lube but are you sure about not using a condom,” the other man asked skeptically.

“I’m clean Cas, I get checked every month and the last person I was with, I made sure they used a condom. Please, I want to really feel you as you fuck me,” the blonde replied.

“I’m going to take such good care of you malen'kiy, you’ll be begging me to cum when I’m finished,” the Russian whispered as he started sucking a hickey onto Dean’s neck.

When Cas was satisfied with the mark, he slowly moved down the blonde’s body, kissing and nipping at the skin along the way. Dean watched him through half lidded eyes, a smile gracing his face.

When Cas reached the man’s cock, he gave it a few strokes before taking the hardened flesh into his mouth. Dean bucked his hips at the heat that surrounded his dick. He moaned as Cas hallowed his cheeks and took him as deep as he could possibly go.

After a few minutes, Cas pulled off with a pop. He shimmied further down Dean’s body and gently tapped on the man’s thighs. Dean got the hint and opened his legs wider, exposing his hole to the other man. He grasped his thighs and held his legs up, allowing Cas the access he needed.

The Russian leaned over and swiped at the furled entrance. Tremors wracked through Dean’s body at the sensation. Cas continued to lick at his entrance before finally slipping his tongue inside. The blonde bucked as his body was flooded with pleasure. The raven continued to lick and prod with his tongue until Dean was a babbling mess.

“Please, Cas, need you in me, please!”

Cas smiled. He wet his own fingers and slipped two inside wanting to make sure Dean was stretched enough. He scissored his fingers stretching the tight muscle further before slipping in a third finger. Once the blonde was stretched enough, he licked his palm before lubing up his own cock.

He climbed back over Dean until his dick was just pushing inside of the other man’s body. He looked down into the beautiful green eyes he was falling for. There was a slight nod and Cas was pushing into the man’s pliant body.

Dean howled in pleasure as the older man slowly sunk into him. Cas slowly pulled out and Dean could feel the drag off the man’s cock against his walls. The skin on skin contact felt exquisite. The Russian filled Dean with long steady thrusts, wanting the younger man to get accustomed to his girth.

The blonde was making noises he had never made as he was filled over and over again. “More, harder, faster,” he muttered on repeat.

Cas sped up his thrusts until he was slamming into the body beneath him. Dean met him thrust for thrust as sweat pooled on both their bodies. The only sounds were their grunts and the sound of the Cas’ balls hitting Dean’s skin.

“So close Cas, so close, please I wanna cum,” the blonde begged.

The Russian reached out and wrapped his hand around Dean’s erection, forming a fist for his cock to move through. With a few more thrusts against his prostate and the feeling of Cas’ palm wrapped around his cock, Dean’s orgasm crashed into him like a freight train. Hot semen erupted from his cock covering his belly in white. He collapsed against the bed as Cas chased his own orgasm.

A couple more thrusts and the Russian was following Dean over the cliff. His eyes were screwed shut even though his mouth hung open. Dean relished in the feel of the man’s cum coating his insides. Cas gave a few more lazy thrusts before pulling out and falling into bed next to Dean. They laid there panting, staring at one another, huge smiles on each of their faces.

Cas got up a few minutes later to clean them up before crawling back into bed. Dean immediately moved into his open arms. Their legs tangled and the Russian wrapped his arms around the assassin. Soon enough, Cas slipped into sleep. Dean lay there, rubbings his fingers lightly up and down the tanned skin.

To a quiet room and a sleeping man, he whispered words he’d never imagine he’d say to someone, “I love you.”

Dean once again found himself heading up the steps to Gabe’s manner although this time he was dressed much more formally in a dark gray suit with a lighter gray button up shirt underneath. Cas was dressed in a dark tan suit with a white undershirt and blue tie that helped to bring out his eyes. He and Dean made for a formidable pair as they walked up the steps. All of Gabe’s staff turned their heads as the two men were escorted into the dining room once again.

This time, when they walked in the room, every set of eyes in the room was watching them. Michael and Lucifer frowned while Gabe raised an eyebrow, obviously impressed. Both of them held their heads high, choosing to stand proud instead of trying to blend in like the last time they were here.

As Dean scanned the room, he noticed he was the only guest from the last party which concerned him. They had assumed if their plan worked, Michael or Lucifer would go after Gabe since the two brothers were close. Now, Dean wasn’t sure if Gabe would be the target. By bringing the blonde back, Cas was letting his brothers know there was another person he had a growing relationship with. Dean preferred it that way though. He would be much better suited to deal with a murderous brother.

When the head waiter called for dinner, Castiel sat at the head of the table instead of Gabe. Dean sat to his right and the other Novak brother to his left with the three women seated next to him. The assassin was barely able to repress his shiver when Michael sat down next to him followed by his guests. Lucifer sat at the other end of the table, his guest sitting next to him. Dean glanced around the table. Michael and Lucifer were glaring daggers at Cas while Gabe had a large grin plastered to his face. The other guests seemed oblivious to the power struggle going on between the brothers.

Throughout the dinner, Dean made sure to keep a steady stream of conversation with Cas and Gabe going. He told the man all about the excursions Cas had taken him on and how much he has enjoyed himself. He made sure to give Cas lots of small touches as dinner progressed. He pretended to have eyes only for the handsome raven even though he was aware of everything occurring in the room.

Dean watched as Lucifer and Michael had slowly grown more and more agitated through dinner. Lucifer’s eyes had narrowed and if he squeezed his glass any harder, it would shatter in his hand. The scowl seemed to be permanently etched on his face. While the blonde Novak’s fury was outward, Michael’s fury simmered just below the surface. He kept a smile on his face and his hands remained loose and relaxed. It was only because Dean was close to the man that he could practically feel the man’s body winding tighter and tighter with tension, a cat ready to pounce.

Everything came to a head during dessert. Gabe asked if Cas had thought anymore about returning home after the threat he had received. Dean waited in anticipation trying to accurately guess which brother had been the cause of Anna’s death.

Cas sat his spoon down and folded his napkin on the table, “Like I said before Gabriel, I have no desire to take over the family business but after much thought and consideration, I have come to the conclusion that I have no choice but to do so.”

Lucifer slammed his hands down and even Michael dropped his silverware in surprise. “What do you mean, you plan on taking over the business Castiel? You’ve never wanted it so why the hell are you going to take it now,” Lucifer shouted.

“I have realized Brother that out of the four of us, I am the most levelheaded and patient so therefore I am the best option. We all know Gabriel has no desire and would be unsuited in running the business. You and Michael have always been so determined to suck up to Father while I was the only one who learned how to make it on his own. I know how to run a business, what do you two know how to do,” Cas challenged his brother.

The vein on Lucifer’s head was about to pop, “You might know how to run a business but you should have lost your rights to this family the day you left for America and broke all connections with us. You are nothing more than a traitor and why Father still holds you on such a pedestal is beyond me!”

Everybody stared at the raging brother in stunned silence. The second oldest Novak was panting from his outburst as he glared at his younger brother.

“Regardless of what you think or how you feel Lucifer, Father will be leaving the business to me and I intend to take it. Your outburst now shows just how unfit you are to take over, maybe if you quit acting like a petulant child, Father might have picked you,” Cas replied stoically.

“You’ll regret this Castiel,” the other man snarled.

Cas leveled his gaze at his brother, “Is that a threat Lucifer?”

“No, it’s a promise,” the Novak brother spat before grabbing his guest around the arm and dragging him behind him as he stormed out the room.

Cas heaved a deep sigh and Dean couldn’t help but reach out and entwine their fingers, trying to comfort the man in any way possible. The raven slowly sat back down, flashing the blonde a quick smile. Cas picked up his spoon and took another bite of his dessert.

They ate the rest of their meal in silence. This time, no one got up and headed for the foyer. As soon as Michael was finished with dinner, he stood up, wished the rest of them a pleasant night, and headed out.

“Ladies, why don’t you go wait for me in my room, I’ll be there in a few minutes,” Gabe said.

The woman quickly left the room not even looking back. Cas stood up and walked away so that he was standing in front of the fireplace. Dean followed him and wrapped an arm around his waist. Cas leaned his cheek on the man’s shoulder.

“I hope you what you know what you’re doing brother. With as mad as Lucifer was, he might just go after you instead of me. As soon as you leave, I will have guards posted outside every door and window. Call me with an update once you know something,” the man said quietly before turning on his heel and walking away.

Cas sighed heavily, feeling as if the weight of the world was on his shoulders.

“I don’t think Gabe will have anything to worry about.”

“Why is that?”

“I think your brothers know that I’m more than just a guest with you. All your other brothers brought different guests than last time and yet I was the one to accompany you. There was a reason I kept touching and smiling at you during dinner and gushing over all the things we’ve done this week,” the blonde replied.

Cas looked at him, horror growing, “You made yourself the target instead of Gabe?”

Dean nodded, “It was better that way.”

“Yes, but we assumed Lucifer would come simply because I wasn’t around, needing me alive to be able to hand the business over. I can’t leave you alone now,” the raven said.

“Yes, you can if you want the plan to succeed,” the blonde argued.

“This wasn’t part of the plan to put you in danger. I promised you at the start of the week that you would be safe, and I meant it. I can’t keep that promise if you’re putting yourself in the line of fire,” Cas disagreed.

Dean’s heart fluttered at how protective the man was being, but he knew this was the best way. He had to say something to get the man to back off. He squeezed his eyes to prevent the tears from falling due to what he was about to say.

He turned so that he was looking at Cas directly, “Well, If I die, then you don’t have to worry about being out of twenty thousand dollars. I’m just a person you hired to fuck so what does my life matter.”

The Russian pulled back as if he had been slapped. Dean watched as sadness flashed through his eyes before it was replaced by a hardness. “Fine, if that’s how you see it then tomorrow I will go to work as usual. Let’s go.”

Dean was glad Cas had turned his back as he couldn’t prevent the single tear that slipped down his cheek. The ride back to the hotel was quiet, neither man saying anything to one another. They slipped from the limo and headed upstairs lost in their thoughts.

Once inside the suite, Cas headed straight for the bedroom. Dean stood there, unsure of what to do. For the first time in his life, he had no idea what to do next. He walked into the bedroom and heard the shower going as he quietly stripped out of his suit before placing it back on the hanger and zipping up the garment bag.

He had just slipped into a pair of boxers when he the water turn off. A few minutes later, the door creaked open and soft footsteps could be heard. Dean stood on his side of the bed as he heard the footsteps get closer.

Suddenly a hand was wrapping around his bicep and spinning him around. A mouth crashed against his painfully, their teeth knocking against one another. Dean didn’t fight it. He let Cas push him on the bed before the man pulled his boxers down and dropped them to the ground. The Russian dropped a condom and lube onto the bed. He grabbed the bottle and squirted some of the slimy substance directly on Dean’s entrance.

He plunged two fingers into the blonde’s body. Dean howled in pain and pleasure as his hands scrabbled to gain purchase against the sheets. Cas was relentless thrusting his fingers in and out and slipping a third one in before the younger man was truly ready. Once he was satisfied, he ripped his fingers out of the other man and quickly rolled a condom on.

He grabbed Dean’s legs and positioned them on his shoulders before shoving his cock deep inside the other man’s body. The blonde’s back bowed as a hoarse shout was ripped from him. Cas was ruthless and he fucked the man beneath him. He had no care for the man beneath, only chasing his own pleasure.

Dean wrapped one hand tightly around Cas’s bicep while the other pumped his cock in time to the Russian’s thrusts. The raven’s thrusts started becoming erratic as he shoved in a few more times before coming deep inside of the assassin. Dean followed seconds after. They remained still, only their rapidly rising and falling chests moving.

As soon as Cas had caught his breath, he pulled out and walked away. Dean watched as he rolled the condom off before throwing it in the garbage can. He disappeared back into the bathroom. He walked back out, body wiped clean, and slipped into bed. Dean sighed heavily before forcing himself up and going to clean up. He crawled into bed a few minutes later and fell into a restless sleep.

The next morning when the blonde woke up, he was alone. He couldn’t say he was surprised. He laid there for a little while, slowly waking up until he finally got out of bed. He walked out and headed straight for the coffee pot. He poured a cup before sitting at the table.

His phone rang and he pulled it out.

“Hey Charlie,” he said in a depressed voice.

“Dean, what happened,” she asked concerned.

The man snorted, “Nothing, except I broke the number one rule. I fell in love with the target.”

“Oh Dean, no. What happened?”

“It doesn’t matter. I’ll be coming home in a day or two and we’ll talk more. I think I’m gonna go for a walk to try and clear my head. I’ll talk to you later.”

“Ok, be careful. I love you,” the redhead tried to console him.

“Love you too Red.”

Dean hung up and finished his coffee before going and getting dressed. He slipped on a pair of jeans and a Henley before lacing up his boots. He slipped his jacket on and was heading for the door when he heard a knock. He went to open it and was shocked to see who stood there.

“Michael, what are you doing here,” Dean asked as he scowled at the man.

The oldest Novak shouldered his way in. He had a furious look on his face as he stopped in the middle of the room and turned to look at the blonde. He ran his hand through his hair before pointing at Dean.

“You, I know you had something to do with my plan going into the fucking trash. Before Castiel met you, he would have never considered taking over the family business,” the man raged as his hands balled into fists.

“What plan, what does it matter if Cas takes over,” Dean asked as he slowly inched towards the kitchen.

“My plan to get Castiel to return home and hand the business over to me. I have been playing the levelheaded brother in all of this trying to be exemplary so that he would choose me over Lucifer. Of course, he had no desire to go home so I tried to give him a push in the right direction,” the man said as he started pacing.

Dean stopped, eyes going wide, “You had Anna killed. No, we were so certain that Lucifer killed her.”

Michael chuckled darkly, “Ha, my brother is many things, but he isn’t the best strategist. He is too hotheaded for things like that but me, I’m the strategizer of the family. I wanted to rule, and I came up with a way to do so. I knew I had to get Cas home so that he could sign the business over because if he didn’t return then Father would have to choose a new successor and after Castiel, Lucifer is the favorite.”

“So, why are you here? Cas already said he isn’t giving the business up, so what can you possibly hope to gain by coming here,” Dean asked as he continued to edge towards the counter.

The oldest Novak smiled sinisterly, “You see, Dean, you’re now part of the plan.”

The assassin regarded the man with caution, “What do you want with me? I’m just some hooker Cas picked up off the street.”

Michael walked over to the table and poured a glass of scotch and took a drink before replying, “A prostitute, my stupid brother fell for a prostitute. Haven’t told Cas the truth, have you Dean?”

The blonde didn’t move, “What are you talking about?”

The other man grinned, “You see, after seeing how engrossed in each other you were last night, I went and did some research. Dean Winchester, orphaned at ten, became a professional assassin for Hunter Corp at eighteen, rose to the top by twenty-one. Or did I get my facts wrong?”

“I still don’t see how I play into all this,” Dean replied, trying to keep his calm.

“My brother cares for you. I threaten to kill you unless Cas hands the business over to me. That’s how you fit into the plan,” Michael said maliciously.

Dean snorted, “We’ve only known each other for a week. There is no love between us, Cas is paying to fuck me and that’s it.”

The other man stood gracefully and walked closer to Dean until he could reach out and run fingers down his cheek before cupping his jaw. The blonde fought the instinct to pull away.

“I’ve never seen my brother look at anyone the way he looks at you. It might have started out as paying you, but it’s morphed into something more. Something I can use to my advantage,” the man purred.

Dean was still for a second longer before he suddenly punched Michael and spun and grabbed a knife from the block he had been creeping towards the whole time. He spun back around to see the other man holding his nose, blood slipping through his fingers and trailing down his hand.

“You bastard, you’ll pay for that,” the man spat as he bent over and pulled a knife from his boot.

He and Dean stood there staring at one another, waiting for the other to make the first move. Michael lunged and the blonde easily avoided and slashed back as the older man sailed past him. Novak cursed as the steel cut through his arm and Dean scurried away as the man slung out blindly.

Their positions were now reversed, Michael close to the counter and Dean against the table. Michael lunged again and the blonde parried the block, knocking the other man’s wrist out of the way before slashing his knife down. He was able to cut the man again, but Michael recovered quicker than he figured, and he shouted out as he felt a blade cut across his shoulder.

Dean shoved the man away from him. As Michael stumbled back, Dean rushed forward, aiming for the man’s stomach. He managed to make a small cut, but Michael mostly avoided the attack. In a move the blonde wasn’t expecting, Novak grabbed his outstretched arm and threw him to the floor. The knife slipped out of Dean’s hand right as Michael was on top of him, the knife plunging downwards.

Dean grabbed the wrist, just barely stopping the knife from plunging into his shoulder. He knew Michael wasn’t trying to kill him, just wanted to injure him bad enough so that he could kidnap him. They fought for a few more minutes when suddenly the older man was ripped off. Dean scrambled to his feet and saw Cas standing there glaring at his brother.

“You, you were the one that killed Anna. Why, how could you,” the younger Novak asked.

“Because I wanted you home so that I could get the business. I knew if you didn’t take over then Father would offer it to Lucifer, and I couldn’t allow that. I’m the one that should be the new don, not you and not Lucifer. Me, I could take the Mafia into the future,” the man said, an edge of madness to his voice.

Cas glanced to Dean, worried because he had never told the blonde any of this. Michael caught the movement and burst out laughing.

“Oh, don’t worry Cas, your little plaything knows all about us I’m sure. You see, Dean there, isn’t normally a prostitute. He’s an assassin and I bet the only reason he was here in the first place, was to kill whoever killed Anna. So, you see, he knows all about us,” the man rambled on.

The raven turned to look at Dean, “Is that true? Is everything he just said true?”

The blonde looked away, “I didn’t come here originally to kill one of you. I came here looking for a target and your family kind of stumbled into my lap.”

“See, Cas, he’s been lying to you this whole time. Now, if you want him to stay alive, why don’t you call Father and tell him to hand the leadership over to me.”

“You think I would still hand it over to you after all of this? After you killed Anna and came here wanting to kill Dean? There is no way in hell I would ever allow the leadership to fall into your hands,” Cas snarled.

“That’s too bad, I really didn’t want to have to kill you. I actually did like you brother,” the man said coldly as he pulled a gun from his pocket and pointed it directly at his brother.

Cas’ eyes went wide, throwing his hands up, not having any other way to defend himself. He waited for the pain of the bullet ripping through his flesh, but it never came. He dropped his hands down to see his brother standing there, a knife protruding from his chest. He watched as the light left his brother’s eyes before the man dropped to the floor dead.

He spun around to see Dean standing there, triumph in his eyes. The blonde immediately pulled his phone and dialed someone.

“Hey Charlie, I need a cleanup crew here ASAP. I’ll fill in you later. Bye.”

He ended the call before dropping his hand down to his side. He looked up at Cas.

“I don’t know what to say,” he started.

“There’s nothing to say Dean. This whole week has been a lie. I was just a target, a means to an end,” the man replied, voice like ice.

Dean crumpled, “No, Cas, it may have started out that way, but I promise, the way I’ve felt, I love you and that’s not a lie.”

“I guess you were telling the truth last night, you were just hired so I could fuck you.”

“Cas, no, I just said that, so the plan didn’t get messed up. You didn’t want me to be the bait and I had to make sure I was,” the man pleaded.

“You need to leave Dean. You need to pack your stuff up and go. I’m going for a walk, long enough for your crew to get here and get things cleaned. I don’t want you here when I return.”

“Cas, please, don’t do this,” he begged, tears slipping down his cheek.

The man paid him no mind. He pulled out his checkbook. He filled a check out, ripped it out the book, and dropped it on the table. He didn’t say another word as he walked to the door. He opened it and paused. Dean thought he might reconsider but then Castiel walked out the door, letting it slam shut with finality.

The blonde stood there, everything inside of him breaking all because of a man he had only met a week ago. He squeezed his eyes closed and let out a sob. He let himself cry for exactly one minute before dried his eyes and went to pack his stuff.

He headed to the bathroom first to take care of his wounds. The worst one was the shoulder wound but even it wasn’t very deep. He quickly wrapped it up before cleaning off a few other scratches and cuts before heading into the bedroom.

He grabbed a suitcase from the closet and packed all of the clothes Cas had bought him. The only ones he left were the suits, not really needing anything as fancy as those. He threw his jacket on last before heading back to the living room. He picked up the check. It was written to him for the sum of twenty thousand, just like they agreed upon. He dropped the check back on the table, readjusted the bag on his shoulder and walked out the door.

He headed down to the lobby, his mind lost in thought. As he was walking out, he ran into Rowena.

“Mr. Winchester, is everything alright?”

“Yeah. Heading home,” he said nonchalantly. He didn’t worry about telling her about the clean up crew on their way. Those people were like ghosts, they were in and out without anyone ever knowing.

She smiled brightly, “Well, I hope you enjoyed your stay and I’m sad to see you go. It’s truly been a pleasure having you stay with us.”

Dean pulled her in for a hug as he replied, “It was great to meet you as well. Thanks for everything. I’ll be getting out your hair now.”

“I can offer you a ride to wherever you need to go,” the woman offered.

The blonde waved her off, “Nah, my car is already here.”

“Well then, goodbye Dean.”

“Bye Rowena.”

The blonde headed outside and to his car. He slid into the seat and went to pull his phone out. He swore as he realized he had left it sitting on the table. He considered going back to get it, but he didn’t want to step foot in that suite again. He put Baby in drive and headed home.

By the time he pulled up to the Roadhouse, he was exhausted. He had driven straight home, choosing not to stop or rest. It was in the wee hours of the morning when Dean walked inside. He trudged upstairs and dropped into bed, letting sleep overtake him.

When he woke up, he was surprised to feel gentle fingers carding through his hair. He opened his eyes to see Ellen sitting on the edge of the bed.

“Good morning hon,” the woman whispered.

Dean flung himself into his aunt’s arms and cried. She wrapped him tight and let tears of her own roll down her cheeks.

In between his sobs, “I’m so sorry for running out like that. It was stupid and irresponsible, and you guys were right; I needed a break. I hope you can forgive me.”

“On honey, of course we forgive you. Your daddy and I just want what’s best for you. We never meant to run you off,” the woman said trying to comfort the crying man.

This was the first time she had seen her boy cry and it had shaken her. She really wasn’t sure what to do but it seemed like she was doing ok. She ran a hand up and down the man’s back trying to call him.

“I’m sorry for always running off and bottling everything up. I should never have done that, and I promise I’m not going to. If you guys tell me I need a break, I’ll take a break. No more working myself to the bone this time of year,” the man promised over and over.

“Dean, hon, what happened to you? Where is all this coming from,” the woman asked curiously.

The blonde pulled away and wiped his eyes. He sat there for a few minutes trying to gather his thoughts. Finally, he told her everything that had transpired over the past week.

As he came to the end he told her the same thing he had told Charlie, “I broke the number one rule, I fell in love with a target.”

“Oh Dean, hon, maybe there’s a way to fix it,” she tried.

The blonde shook his head, “No, there’s not. I lied to Cas the whole week about who and what I was. He couldn’t even look at me as he walked out. I’m pretty sure if he never sees me again, it’ll be too soon.”

“If he cares about you the way you care about him, he’ll come around, I promise,” the woman said reassuringly.

Dean shrugged, “It is what it is Ellen. I just wanna try and forget about it.”

Ellen decided to not say anything more, “There’s breakfast down in the kitchen waiting for you, if you want it. Bobby and Jo are excited to see you as well, so at least come down and see them.”

“I will.”

She placed a tender kiss on his forehead before walking out. The next couple of weeks, Dean was in a slump. He didn’t take any more cases, knowing he wouldn’t be able to focus. He mainly stayed in his room staring out the window overlooking the place, not that there was much to look at. The Roadhouse had been built in a pretty small town, easier to keep secrets like that.

A few of his buddies from H.C. tried to get him to hang out but he denied any invitation. Jo tried to entice him to play some pool or go see a movie in a nearby town, but he would shake his head and climb the stairs to his room. She had asked if he wanted to go see the new Marvel movie and Dean had barely made it to his room before the tears fell.

One night, about three weeks after he had left Beverly Hills, Dean was sitting downstairs at the bar, sipping on a glass of whiskey. Jo had dragged him down, refusing to take no for an answer.

“Jo, why can’t I just sit in my room,” the man grumbled as he took a seat.

“Dean, you need to get out, go do something, you’re wasting away up there,” the younger girl snapped at him.

“Whatever, can I get a shot of whiskey?”

She filled a cup and sat it in front of him. He looked around the bar and it seemed like the place was mocking him. Everywhere he looked, it seemed like people were hooking up for the night. He drained his glass before standing up and heading outside. He walked to where Baby was parked and sat on her hood. He looked at the stars above him.

“I wish you guys were here,” the blonde lamented.

He heard a car pull up in the distance but paid no mind, continuing to look at the stars. He closed his eyes and breathed deeply, trying to calm himself. He heard the person’s footsteps get closer but still kept his eyes shut.

“Hello malen'kiy.”

His eyes opened wide and he shot up to come face to face with the man he had been dreaming about for weeks. He stood directly in front of Dean, more casually dressed than he’d ever seen him. Dean felt his heartrate pick up as he stared at the blue-eyed beauty.

“What are you doing here Cas,” he asked breathlessly.

The man gave a small smile before pulling Dean’s phone out of his pocket. “I came to return this to you. I thought you might be missing it.”

He held the phone out and the blonde took it. Dean cradled it between his hands, not really knowing what else to do with it.

“Thanks, but you know, you could have just thrown it away. I’ve already got a new one so, uh, yeah,” he finished lamely.

“I was worried you might have pictures or other important info that might hav…”

“What are you doing here Cas,” the man asked again. “The real reason, not some shitty excuse of wanting to return my phone.”

Cas lifted his hand before dropping it back to his side, “I hate the way we left things Dean. These past few weeks, I haven’t been able to get you out my mind.”

The assassin shrugged, “Good to know I’m not the only one losing sleep, I guess.”

“Why didn’t you take the check Dean? That was the deal, you stay with me for the week and help me find Anna’s killer and in return, I’d pay you twenty-thousand dollars. So, why did you leave it sitting on the table of my suite,” the man asked.

Dean looked away, “That’s how it started but that wasn’t how it ended.”

“So, how did it end,” the man asked as he took a step closer.

The blonde locked eyes with the other man, “It ended with you finding out who I really was. It ended with me falling in love with you, but you left anyways. I couldn’t take the money because if I did, then it just made it seem like the whole thing was meaningless. Maybe it was for you but for me, it was the best week of my entire life,” Dean replied sadly.

Cas stepped even closer, their knees bumping, “You didn’t get the whole ending right.”

The blonde quirked an eyebrow, “No? What part did I leave out?”

The Russian reached up and cupped the man’s jaw, “The part where from the moment I walked out that suite, I regretted it. The part where I fell in love right back.”

Dean pulled away, sliding off his car and moving until they were standing a few feet apart, “I thought we would be done with the lies. I heard what you said Cas. I tried to tell you the truth and you didn’t want to hear it.”

“How did I know that wasn’t another lie Dean? The whole week I thought something was forming between us and then at Gabe’s you tell me you were just a hired fuck.”

“I was trying to convince you to let me be the bait so that our whole plan didn’t get ruined. I hated saying it, but I had to. But you didn’t have to take me back to the suite and fuck me like I meant nothing to you. It was the one time you actually made me feel like I was just a hired fuck,” the blonde said defeatedly.

“I’m sorry for the way that I treated you that night. It was extremely shitty.”

“Yeah, well, it was pretty shitty of me not to tell you the truth.”

“Will you tell me the truth now,” the Russian asked, a spark of hope in his eyes.

“I’m a paid assassin working for a government organization called Hunter Corp. I was looking for a target trying to throw myself into work, so I didn’t think about the anniversary of my family’s death. When I saw you in the club, I was immediately attracted to you and wanted to sleep with you even if you didn’t turn out to be a target. When you offered me the money, there was no way I could say no especially since I was going to be able to do my job in the process. That’s all the week was supposed to be, help you figure out which brother killed your sister and take him out. If I got fucked by you throughout the week, that was just a bonus.”

Dean walked closer until they were standing toe to toe. He reached out and wound his fingers with Cas’. He was overjoyed when the man didn’t pull away.

They locked eyes as Dean continued his story, “I was supposed to spend the week with you, kill your brother, take the money, and return home. I wasn’t supposed to enjoy myself, to like you, to fall in love with you. But I did and I can’t nor would I want to take it back. You’ve changed me Cas and I will never be that person I was before I met you. I know what it feels like to be in love now.”

Cas brought his hands up to cup the blonde’s cheeks. He stroked across the skin with his thumbs as their eyes remained locked on one another, “I love you too. I’m sorry it took me so long.”

Dean covered one of the Russian’s hands with his own, “You came back, that’s all that matters.”

They both pushed forward, and their lips met in the middle. Dean wound his arms around Cas’ waist and pulled him closer. One of the raven’s hands moved to cup the back of Dean’s neck while the other rested heavily on the man’s hip. Their lips moved against each other and when the blonde opened his mouth a fraction, Cas swooped inside. Dean felt himself melting deeper into the kiss.

Each man let all of his pent-up emotions flow through the kiss. Their joy and anger, their happiness and fury, but most importantly their love. When they broke apart, they rested their foreheads against one another as they stared into each other’s eyes.

“So, where do we go from here,” the blonde asked.

“Wherever you want.”

1 Year Later

Dean stared at the lifeless body on the floor, no remorse in his gaze. It was eighteen years too late, but the assassin had finally found the bastard who had killed his family. With Cas’ money and some outside help, they were able to reopen the case file and figure who had killed Sam and his parents. As soon as the man’s location had been discovered, Dean had went after him.

He pulled his phone out. He typed a quick message to Charlie, letting her know to send in the clean up crew. He wiped his knife clean before grabbing his jacket off the chair and putting it on before heading outside to Baby.

A few hours later, he returned to the home he shared with Cas. It had taken a few months for them to figure out the dynamic of their relationship, but they were going strong as ever. Cas had moved the head of his corporation to Nebraska where the Roadhouse was located so that Dean could still be close to his family. They had purchased a house only twenty minutes away from Dean’s family so he could visit them whenever he wanted.

He no longer worked as an assassin full time. He took on one or two cases a month and usually they were close by. He now worked mostly at the Roadhouse, either cooking or working at the bar. He also served as the encyclopedia for H.C. with assassins coming to him when they needed help or guidance on their case.

He was glad Cas had never asked him to fully give up being an assassin, but he had asked for Dean to cut back on the cases. The blonde had been amenable, wanting to finally have a life instead of always on the road, trying to kill someone. He didn’t like being away from his boyfriend no more than Cas did.

As he walked inside, he dropped Baby’s keys in the bowl on the little table before heading upstairs. It was late and figured his boyfriend would be nestled in bed watching TV or reading a book. He got to their bedroom and stood in the frame watching the Russian read. Cas finally looked up and smiled when he realized he was being watched.

“Hello malen'kiy.”

Dean stripped as he walked to the bed, crawling underneath the covers completely naked as he curled up next to his boyfriend.

“He’s dead Cas, the bastard is finally dead,” the man whispered.

“How do you feel?”

The blonde shrugged, “I don’t know. I thought I would be happy to get my revenge but now, I’m just glad he can’t hurt anyone ever again.”

“I think it’s because you came to term with their deaths. He was now just another target,” the Russian tried to explain.

Dean pulled the other man until he was lying on top of him, “I don’t know and maybe I never will. I don’t want think about that right now. All I want to think about is you showing me how much you love me.”

Cas smiled before pressing a tender kiss to his boyfriend’s lips. Dean wrapped his arms around the older man’s neck as they kissed. Cas licked along the seam of his lips and he opened readily, letting the man inside. The Russian ran his hands up and down Dean’s body with featherlight touches causing his skin to break out in goosebumps.

Cas broke away and started kissing down his boyfriend’s body. He gave a few nips causing Dean to flinch and whimper. He loved the little blossoms of pain Cas’ bites caused. The man kissed down to his waist and continued his trail until coming to the blonde’s pelvis. He pulled away before touching Dean’s hardened flesh.

The blonde whined, “Cas, c’mon babe.”

“Patience malen'kiy, I’ve got to grab the lube.”

Once he had the bottle, he went back to where he was, this time not pausing to take Dean’s dick in his mouth. The blonde arched as his flesh was encompassed in the slick wet heat of Cas’ mouth. His hands fisted in the short black locks as he tried to keep his hips still. He jerked when he felt a slick finger probe at his entrance.

Cas teased the tight flesh for a moment before finally slipping inside causing Dean to moan in pleasure. The Russian moved with care, wanting his boyfriend to be stretched before adding another finger and then another. By the time Cas had three fingers moving smoothly in and out of Dean, the blonde was a quivering mess. All the while, Cas had continued to suck on the blonde’s cock bringing him closer to the edge. He finally pulled off with a pop and pulled his fingers out.

Dean groaned at the feeling of being empty, “Cas, please babe, I need you. I want to feel you fill me. Need you inside of me.”

Cas pressed a gentle kiss to his lips before guiding his legs to wrap around his waist and position his cock at Dean’s slick entrance. He locked eyes with his boyfriend as he slowly pushed in, letting the blonde get used to the stretch of being filled.

Dean couldn’t stop the buck of his hips, causing Cas’ cock to fill him more. Once the Russian was fully seated inside of Dean, he leaned over and locked his hands with the blonde’s pushing them into the bed. He then slowly started pumping in and out, making sure his boyfriend would feel the drag of his cock against his sensitive walls.

The man dropped his head against Dean’s chest as the blonde’s hole squeezed around him, increasing his pleasure. “So tight malen'kiy, feel so good wrapped around me. Love you so much.”

Dean panted, “Love you too babe, now please more, I need more.”

The Russian increased the speed and power of his thrusts until he was slamming into the blonde over and over, making sure to rub against his prostate with every thrust. Dean thrashed his head as his body was assaulted with pleasure. Every time Cas hit his prostate, sparks of fire travelled through his veins, lighting his blood aflame.

“Cas, close, babe, so close, please touch me,” the blonde begged on the brink of orgasm.

The raven pulled a hand away to wrap it around Dean’s leaking flesh and started pumping in time to his thrusts. Dean howled in pleasure as he wrapped an arm around the older man’s neck and pulled him in for a passionate kiss. Their tongues tangled together as they explored each other’s mouth.

Cas slammed in harder, sending more waves of pleasure crashing through the younger man. With a jerk of his wrist on Dean’s cock and one last thrust that rammed into the blonde’s prostate, Dean keened high in his throat as he came. Dean watched as his boyfriend’s eyes closed and his mouth hung open as his orgasm rushed through him. With Dean’s body clamping down tight around him, a few more thrusts and Cas was cumming deep inside his boyfriend.

Cas pulled out, his cum leaking out of Dean’s hole. He couldn’t help but push his cock back into Dean a few times, making a mess of his entrance. Finally, the Russian’s limbs gave out and he collapsed next to Dean. The blonde immediately curled into him.

“That was fucking fantastic,” Dean murmured.

“I have to concur.”

Dean snuggled closer, obviously on the brink of sleep, “Love you Cas.”

The raven smiled as the blonde’s soft snores filled the room. He got up and quickly cleaned them off before joining his boyfriend back in bed. He wrapped around Dean before pulling the covers over them.

He placed a tender kiss to the blonde’s forehead, “I love you too malen'kiy.”

**Notes for the Chapter:**

> And it's all wrapped up. I know in the movie they go to the Opera but I couldn't see Cas taking Dean to the Opera. Hope you guys have enjoyed this story as much as I have.

**Author's Note:**

> There's the first chapter! Please leave a kudos or comment to tell me what you think.


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